Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Stereoselective Access to Highly Substituted Vinyl Ethers via trans-Difunctionalization of Alkynes with Alcohols and Iodine(III) Electrophile

  • Wei Ding
    Wei Ding
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    More by Wei Ding
  • Jinkui Chai
    Jinkui Chai
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. China
    More by Jinkui Chai
  • Chen Wang
    Chen Wang
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    Zhejiang Key Laboratory of Alternative Technologies for Fine Chemical Process, Shaoxing University, Shaoxing 312000, P. R. China
    More by Chen Wang
  • Junliang Wu*
    Junliang Wu
    College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. China
    *E-mail: [email protected]
    More by Junliang Wu
  • , and 
  • Naohiko Yoshikai*
    Naohiko Yoshikai
    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
    *E-mail: [email protected]
Cite this: J. Am. Chem. Soc. 2020, 142, 19, 8619–8624
Publication Date (Web):May 3, 2020
https://doi.org/10.1021/jacs.0c04140
Copyright © 2020 American Chemical Society

    Article Views

    8846

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (5)»

    Abstract

    Abstract Image

    A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c04140.

    • Experimental procedures and characterization data for all the new products (PDF)

    • Crystallographic data for 4ba (CIF)

    • Crystallographic data for 4na (CIF)

    • Crystallographic data for 6aa (CIF)

    • Crystallographic data for 6la (CIF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 71 publications.

    1. Li Wei, Yanhui Guo, Ziyang Li, Huanfeng Jiang, Chaorong Qi. Silver-Catalyzed Coupling of Ethynylbenziodoxolones with CO2 and Amines to Afford O-β-Oxoalkyl Carbamates. Organic Letters 2024, 26 (22) , 4600-4605. https://doi.org/10.1021/acs.orglett.4c01147
    2. Chloe G. Williams, Sepand K. Nistanaki, Krista Dong, Woojin Lee, Kendall N. Houk, Hosea M. Nelson. Main Group-Catalyzed Cationic Claisen Rearrangements via Vinyl Carbocations. Organic Letters 2024, Article ASAP.
    3. Chisaki Arakawa, Kazuya Kanemoto, Katsuya Nakai, Chen Wang, Shunya Morohashi, Eunsang Kwon, Shingo Ito, Naohiko Yoshikai. Carboiodanation of Arynes: Organoiodine(III) Compounds as Nucleophilic Organometalloids. Journal of the American Chemical Society 2024, 146 (6) , 3910-3919. https://doi.org/10.1021/jacs.3c11524
    4. Deepak Bhadoria, Rajesh Kumar, Ruchir Kant, Atul Kumar. Regio- and Stereoselective Intermolecular Oxysulfonylation of Alkynes with 1,3-Diketones to Access (Z)-β-Sulfonated Enethers. The Journal of Organic Chemistry 2023, 88 (19) , 13666-13677. https://doi.org/10.1021/acs.joc.3c01345
    5. Shuma Sasaki, Jun Kikuchi, Shingo Ito, Naohiko Yoshikai. Stereoselective Approach to Multisubstituted Enolates from Unactivated Alkynes: Oxyalkylidenation of Alkynyl Ketone Enolates with Aldehydes. The Journal of Organic Chemistry 2023, 88 (19) , 14096-14104. https://doi.org/10.1021/acs.joc.3c01615
    6. Joseph A. Kaplan, Suzanne A. Blum. Iodination–Group-Transfer Reactions to Generate Trisubstituted Iodoalkenes with Regio- and Stereochemical Control. The Journal of Organic Chemistry 2023, 88 (18) , 13236-13247. https://doi.org/10.1021/acs.joc.3c01495
    7. San L. Pham, Taehee Kim, Frank E. McDonald. Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides. Organic Letters 2023, 25 (28) , 5297-5301. https://doi.org/10.1021/acs.orglett.3c01849
    8. Thomas Duhamel, Simone Scaringi, Baptiste Leforestier, Amalia I. Poblador-Bahamonde, Clément Mazet. Assisted Tandem Pd Catalysis Enables Regiodivergent Heck Arylation of Transiently Generated Substituted Enol Ethers. JACS Au 2023, 3 (1) , 261-274. https://doi.org/10.1021/jacsau.2c00645
    9. Zhantao Yang, Shenyin Hou, Yunfan Cheng, Li Sun, Chun-Hua Yang. Co-Catalyzed Reductive Cyclization of Acrylate-Containing 1,6-Enynes. The Journal of Organic Chemistry 2022, 87 (19) , 13339-13345. https://doi.org/10.1021/acs.joc.2c01345
    10. Jun Kikuchi, Kaito Maesaki, Shuma Sasaki, Weifan Wang, Shingo Ito, Naohiko Yoshikai. Stereoselective Synthesis of β-Alkoxy-β-amido Vinylbenziodoxoles via Iodo(III)etherification of Ynamides. Organic Letters 2022, 24 (38) , 6914-6918. https://doi.org/10.1021/acs.orglett.2c02570
    11. Chang-Sheng Wang, Ploypailin Siew Ling Tan, Wei Ding, Shingo Ito, Naohiko Yoshikai. Regio- and Stereoselective Synthesis of Enol Carboxylate, Phosphate, and Sulfonate Esters via Iodo(III)functionalization of Alkynes. Organic Letters 2022, 24 (1) , 430-434. https://doi.org/10.1021/acs.orglett.1c04123
    12. Chunngai Hui, Lukas Brieger, Carsten Strohmann, Andrey P. Antonchick. Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines. Journal of the American Chemical Society 2021, 143 (45) , 18864-18870. https://doi.org/10.1021/jacs.1c10175
    13. Ashish Kumar Sahoo, Anjali Dahiya, Bubul Das, Ahalya Behera, Bhisma K. Patel. Visible-Light-Mediated Difunctionalization of Alkynes: Synthesis of β-Substituted Vinylsulfones Using O- and S-Centered Nucleophiles. The Journal of Organic Chemistry 2021, 86 (17) , 11968-11986. https://doi.org/10.1021/acs.joc.1c01350
    14. Yajie Yang, Lu Cheng, Mengdan Wang, Liqiang Yin, Ye Feng, Chengyu Wang, Yanzhong Li. Difunctionalization of Alkynones by Base-Mediated Reaction with α,α-Dithioketones. Organic Letters 2021, 23 (14) , 5339-5343. https://doi.org/10.1021/acs.orglett.1c01640
    15. Roshayed Ali Laskar, Wei Ding, Naohiko Yoshikai. Iodo(III)-Meyer–Schuster Rearrangement of Propargylic Alcohols Promoted by Benziodoxole Triflate. Organic Letters 2021, 23 (3) , 1113-1117. https://doi.org/10.1021/acs.orglett.1c00039
    16. Chonglong He, Min Wang, Yulong Wang, Lirong Zhao, Youkang Zhou, Keyuan Zhang, Shenyu Shen, Yaqiong Su, Xin-Hua Duan, Le Liu. Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent. Science China Chemistry 2024, 67 (6) , 2022-2028. https://doi.org/10.1007/s11426-023-1930-6
    17. Sayad Doobary, Berit Olofsson. Cyclopropenium functionalization. Nature Chemistry 2024, 16 (6) , 847-848. https://doi.org/10.1038/s41557-024-01541-w
    18. Jun Kikuchi, Toya Nagata, Shingo Ito, Naohiko Yoshikai. Three-component Friedel–Crafts-type difunctionalization of ynamides with (hetero)arenes and iodine( iii ) electrophile. Organic Chemistry Frontiers 2024, 11 (11) , 3072-3079. https://doi.org/10.1039/D4QO00489B
    19. Kazuya Kanemoto, Ken Yoshimura, Koki Ono, Wei Ding, Shingo Ito, Naohiko Yoshikai. Amino‐ and Alkoxybenziodoxoles: Facile Preparation and Use as Arynophiles. Chemistry – A European Journal 2024, 30 (29) https://doi.org/10.1002/chem.202400894
    20. Hui Han, Glen Wee Zhuan Goh, Yongxin Li, Naohiko Yoshikai, Shingo Ito. 1, 3‐Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides and Alkynylbenziodoxoles for Synthesis of Functional Dibenzoullazines †. Chinese Journal of Chemistry 2024, 42 (10) , 1079-1083. https://doi.org/10.1002/cjoc.202300637
    21. Ravi Kumar, Toshifumi Dohi, Viktor V. Zhdankin. Organohypervalent heterocycles. Chemical Society Reviews 2024, 53 (9) , 4786-4827. https://doi.org/10.1039/D2CS01055K
    22. Zhong‐Tao Jiang, Zhengzhao Chen, Ying Xia. Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis. Angewandte Chemie International Edition 2024, 63 (11) https://doi.org/10.1002/anie.202319647
    23. Zhong‐Tao Jiang, Zhengzhao Chen, Ying Xia. Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis. Angewandte Chemie 2024, 136 (11) https://doi.org/10.1002/ange.202319647
    24. Sayad Doobary, Ester Maria Di Tommaso, Alexandru Postole, A. Ken Inge, Berit Olofsson. Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols. Frontiers in Chemistry 2024, 12 https://doi.org/10.3389/fchem.2024.1376948
    25. Haoru Jin, Wei Shi, Chao Zhou, Hongji Li, Lei Wang, Tao Miao. Direct Synthesis of ( E )‐ β ‐(Thiocyanato)vinyl Sulfones by 1,2‐Difunctionalization of Alkynes with Sulfinic Acids and Potassium Thiocyanate. Advanced Synthesis & Catalysis 2024, 366 (3) , 426-430. https://doi.org/10.1002/adsc.202301229
    26. Paloma Mingueza-Verdejo, Jose Pedro Cerón-Carrasco, Judit Oliver-Meseguer, Antonio Leyva-Pérez. A Formal Exchange Reaction between Ketones and Vinyl Ethers with Solid Catalysts. Synthesis 2024, 56 (03) , 455-461. https://doi.org/10.1055/a-2204-2801
    27. Hanliang Zheng, Gangguo Zhu. Controllable Synthesis of Fully-Substituted Alkyl Vinyl Ethers Enabled by Dual-Functional Copper Catalysis. Chinese Journal of Organic Chemistry 2024, 44 (3) , 1043. https://doi.org/10.6023/cjoc202400017
    28. Ilias Koutsopetras, Abhaya Kumar Mishra, Rania Benazza, Oscar Hernandez‐Alba, Sarah Cianférani, Guilhem Chaubet, Stefano Nicolai, Jérôme Waser. Cysteine‐Cysteine Cross‐Conjugation of both Peptides and Proteins with a Bifunctional Hypervalent Iodine‐Electrophilic Reagent. Chemistry – A European Journal 2023, 29 (70) https://doi.org/10.1002/chem.202302689
    29. Jiaqiong Sun, Yunliang Guo, Jiuli Xia, Guangfan Zheng, Qian Zhang. Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents. Molecules 2023, 28 (21) , 7420. https://doi.org/10.3390/molecules28217420
    30. Lijun Chang, Cheng Cai, Ran Chen, Jianhui Chen, Yanshu Luo, Yuanzhi Xia. Ligand-controlled cobalt-catalyzed isomerization and reductive C–O bond cleavage of allylic ethers. Organic Chemistry Frontiers 2023, 10 (18) , 4643-4648. https://doi.org/10.1039/D3QO00852E
    31. Mengdan Wang, Lu Cheng, Junying Ma, Weiwei Lu, Junling Wang. Base‐Promoted Difunctionalization of Alkynes: One‐Pot Synthesis of Polysubstituted Chromones. European Journal of Organic Chemistry 2023, 26 (32) https://doi.org/10.1002/ejoc.202300456
    32. Tobias Michael Milzarek, Jerome Waser. Synthese von Trifluormethylierten Alkenen: hypervalentes Iod trifft hochvalentes Kupfer. Angewandte Chemie 2023, 135 (33) https://doi.org/10.1002/ange.202306128
    33. Tobias Michael Milzarek, Jerome Waser. Synthesis of Trifluoromethylated Alkenes: Hypervalent Iodine Meets High‐Valent Copper. Angewandte Chemie International Edition 2023, 62 (33) https://doi.org/10.1002/anie.202306128
    34. Mohana Reddy Mutra, Jing Li, Jeh-Jeng Wang. Light-mediated sulfonyl-iodination of ynamides and internal alkynes. Chemical Communications 2023, 59 (43) , 6584-6587. https://doi.org/10.1039/D3CC00842H
    35. Kumar Bhaskar Pal, Ester Maria Di Tommaso, A. Ken Inge, Berit Olofsson. Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides**. Angewandte Chemie 2023, 135 (20) https://doi.org/10.1002/ange.202301368
    36. Kumar Bhaskar Pal, Ester Maria Di Tommaso, A. Ken Inge, Berit Olofsson. Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides**. Angewandte Chemie International Edition 2023, 62 (20) https://doi.org/10.1002/anie.202301368
    37. Monika Sihag, Rinku Soni, Neha Rani, Mayank Kinger, Deepak Kumar Aneja. Recent Synthetic Applications of Hypervalent Iodine Reagents. A Review in Three Installments: Installment III. Organic Preparations and Procedures International 2023, 55 (3) , 199-242. https://doi.org/10.1080/00304948.2022.2114239
    38. Irina A. Mironova, Dmitrii M. Noskov, Akira Yoshimura, Mekhman S. Yusubov, Viktor V. Zhdankin. Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications. Molecules 2023, 28 (5) , 2136. https://doi.org/10.3390/molecules28052136
    39. Tian-Shu Zhang, Si-Qing Song, Meng-Jiao Qi, Wen-Juan Hao, Bo Jiang. Photocatalytic annulative trifluoromethyletherification of 1,6-enynes for accessing 1-indanones. Tetrahedron Letters 2023, 114 , 154290. https://doi.org/10.1016/j.tetlet.2022.154290
    40. Chaoxing Cui, Jianli Wu, Xixi Song, Miaomiao Li. Synthesis of para-Quinone Methides via Oxidative Ring-Opening of Spiro-cyclopropanyl-cyclohexadienones. Synthesis 2022, 54 (21) , 4802-4809. https://doi.org/10.1055/a-1878-8272
    41. Naohiko Yoshikai. Exploring New Reactions and Syntheses of Trivalent Iodine Compounds. Journal of Synthetic Organic Chemistry, Japan 2022, 80 (11) , 1011-1018. https://doi.org/10.5059/yukigoseikyokaishi.80.1011
    42. Mingyu Liu, Juntao Sun, Tao Zhang, Yi Ding, Ye‐Qiang Han, Raúl Martín‐Montero, Yu Lan, Bing‐Feng Shi, Keary M. Engle. Regio‐ and Stereoselective 1,2‐Oxyhalogenation of Non‐Conjugated Alkynes via Directed Nucleopalladation: Catalytic Access to Tetrasubstituted Alkenes**. Angewandte Chemie 2022, 134 (43) https://doi.org/10.1002/ange.202209099
    43. Mingyu Liu, Juntao Sun, Tao Zhang, Yi Ding, Ye‐Qiang Han, Raúl Martín‐Montero, Yu Lan, Bing‐Feng Shi, Keary M. Engle. Regio‐ and Stereoselective 1,2‐Oxyhalogenation of Non‐Conjugated Alkynes via Directed Nucleopalladation: Catalytic Access to Tetrasubstituted Alkenes**. Angewandte Chemie International Edition 2022, 61 (43) https://doi.org/10.1002/anie.202209099
    44. Guang’an Zhang, Peng Huang, Zhaoxia Li, Jing Guo, Yonghong Pei, Miaomiao Li, Wei Ding, Junliang Wu. Copper-catalyzed enantioselective decarboxylative cyanation of β,γ-unsaturated carboxylic acids to access chiral allyl nitriles. Cell Reports Physical Science 2022, 3 (10) , 101104. https://doi.org/10.1016/j.xcrp.2022.101104
    45. Tong Li, Chaoxing Cui, Yuxia Zhang, Xixi Song, Zechao Wang, Junbiao Chang. 2-Iodoxybenzoic Acid–Dimethyl Sulfoxide (IBX-DMSO)-Promoted Oxidative Aromatization of Spiro[2.5]octa-4,7-dien-6-one. Synlett 2022, 33 (15) , 1546-1550. https://doi.org/10.1055/a-1863-8862
    46. Jun Li, Chuang Zhou, Hong Liang, Xiao‐Qiang Guo, Lian‐Mei Chen, Tai‐Ran Kang. Direct One‐Pot Construction of Diaryl Thioethers and 1,3‐Diynes through a Copper(I)‐Catalyzed Reaction of λ 3 ‐Iodanes with Thiophenols. European Journal of Organic Chemistry 2022, 2022 (30) https://doi.org/10.1002/ejoc.202200613
    47. Shun‐Dong He, Xiao‐Qiang Guo, Jun Li, Yu‐Cheng Zhang, Lian‐Mei Chen, Tai‐Ran Kang. Base‐Promoted Reaction of Phenols with Spirocylic λ 3 ‐Iodanes: Access to Both 2‐Iodovinyl Aryl Ethers and Diaryl Ethers. European Journal of Organic Chemistry 2022, 2022 (26) https://doi.org/10.1002/ejoc.202200516
    48. Zhiwen Nie, Huifang Lv, Tonglin Yang, Miaodong Su, Weiping Luo, Qiang Liu, Cancheng Guo. Synthesis of Non‐Terminal Alkenyl Ethers, Alkenyl Sulfides, and N‐Vinylazoles from Arylaldehydes or Diarylketones, DMSO and O, S, N‐Nucleophiles. Advanced Synthesis & Catalysis 2022, 364 (8) , 1473-1480. https://doi.org/10.1002/adsc.202200020
    49. Mikus Puriņš, Jerome Waser. Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary. Angewandte Chemie 2022, 134 (11) https://doi.org/10.1002/ange.202113925
    50. Mikus Puriņš, Jerome Waser. Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary. Angewandte Chemie International Edition 2022, 61 (11) https://doi.org/10.1002/anie.202113925
    51. Guang’an Zhang, Peng Huang, Zhaoxia Li, Jing Guo, Yonghong Pei, Miaomiao Li, Wei Ding, Juliang Wu. Copper-Catalyzed Enantioselective Decarboxylative Cyanation of β,γ-Unsaturated Carboxylic Acids to Access Chiral Allyl Nitriles. SSRN Electronic Journal 2022, 53 https://doi.org/10.2139/ssrn.4147934
    52. Yu Zheng, Shencheng Qian, Pengcheng Xu, Binnan Zheng, Shenlin Huang. Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes. Chinese Journal of Organic Chemistry 2022, 42 (12) , 4275. https://doi.org/10.6023/cjoc202209041
    53. Jinkui Chai, Wei Ding, Chen Wang, Shingo Ito, Junliang Wu, Naohiko Yoshikai. Ritter-type iodo( iii )amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides. Chemical Science 2021, 12 (45) , 15128-15133. https://doi.org/10.1039/D1SC05240C
    54. Jonathan K. Sader, Bryce A. Molder, Jeremy E. Wulff. A Chan–Evans–Lam approach to trisubstituted vinyl ethers. Organic & Biomolecular Chemistry 2021, 19 (44) , 9649-9653. https://doi.org/10.1039/D1OB01827B
    55. Akira Yoshimura, Christopher D. Huss, Akio Saito, Tsugio Kitamura, Viktor V. Zhdankin. 2-Iodosylbenzoic acid activated by trifluoromethanesulfonic anhydride: efficient oxidant and electrophilic reagent for preparation of iodonium salts. New Journal of Chemistry 2021, 45 (36) , 16434-16437. https://doi.org/10.1039/D1NJ03787K
    56. Lu Wang, Fuxing Shi, Chaorong Qi, Wenjie Xu, Wenfang Xiong, Bangxiong Kang, Huanfeng Jiang. Stereodivergent synthesis of β-iodoenol carbamates with CO 2 via photocatalysis. Chemical Science 2021, 12 (35) , 11821-11830. https://doi.org/10.1039/D1SC03366B
    57. Sondes Ghrairi, Khaled Essalah, Benoit Crousse, Thouraya Barhoumi-Slimi. β-chlorovinylaldehydes as intermediates in the synthesis of new substituted β–fluoroalkoxyvinyl aldehydes and corresponding alcohols. Journal of Fluorine Chemistry 2021, 248 , 109837. https://doi.org/10.1016/j.jfluchem.2021.109837
    58. Akira Yoshimura, Christopher D. Huss, Mackenzie Liebl, Gregory T. Rohde, Scott M. Larson, Gunnar B. Frahm, Mattew W. Luedtke, Tanner J. Schumacher, Zachary S. Gardner, Viktor V. Zhdankin, Pavel S. Postnikov, Mekhman S. Yusubov, Tsugio Kitamura, Akio Saito. Preparation, Structure, and Reactivity of Pseudocyclic β‐Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives. Advanced Synthesis & Catalysis 2021, 363 (13) , 3365-3371. https://doi.org/10.1002/adsc.202100341
    59. Peter‐Yong Wang, Itai Massad, Ilan Marek. Stereoselective Sc(OTf) 3 ‐Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals. Angewandte Chemie 2021, 133 (23) , 12875-12879. https://doi.org/10.1002/ange.202101634
    60. Peter‐Yong Wang, Itai Massad, Ilan Marek. Stereoselective Sc(OTf) 3 ‐Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals. Angewandte Chemie International Edition 2021, 60 (23) , 12765-12769. https://doi.org/10.1002/anie.202101634
    61. Takuya Matsumoto, Hiroshi Hagiyama, Kanetsugu Kuribayashi, Kazuhito Hioki, Hikaru Fujita, Masahito Ochiai, Munetaka Kunishima. A versatile iodo( iii )etherification of terminal ethynylsilanes using BF 3 –O i Pr 2 and alkyl benzyl ethers. Organic & Biomolecular Chemistry 2021, 19 (17) , 3825-3828. https://doi.org/10.1039/D1OB00479D
    62. Daisuke Shimbo, Toshifumi Maruyama, Norihiro Tada, Akichika Itoh. N -Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis -enamides through vinyl benziodoxolones. Organic & Biomolecular Chemistry 2021, 19 (11) , 2442-2447. https://doi.org/10.1039/D1OB00055A
    63. Rong Ye, Jing Sun, Ying Han, Chao-Guo Yan. Molecular diversity of TEMPO-mediated cycloaddition of ketohydrazones and 3-phenacylideneoxindoles. New Journal of Chemistry 2021, 45 (11) , 5075-5080. https://doi.org/10.1039/D0NJ06036D
    64. Yasushi Yoshida, Seitaro Ishikawa, Takashi Mino, Masami Sakamoto. Bromonium salts: diaryl-λ 3 -bromanes as halogen-bonding organocatalysts. Chemical Communications 2021, 57 (20) , 2519-2522. https://doi.org/10.1039/D0CC07733J
    65. Tomoki Ura, Daisuke Shimbo, Masaharu Yudasaka, Norihiro Tada, Akichika Itoh. Synthesis of Phenol‐Derived cis ‐Vinyl Ethers Using Ethynyl Benziodoxolone. Chemistry – An Asian Journal 2020, 15 (23) , 4000-4004. https://doi.org/10.1002/asia.202001102
    66. Nina Declas, Guillaume Pisella, Jerome Waser. Vinylbenziodoxol(on)es: Synthetic Methods and Applications. Helvetica Chimica Acta 2020, 103 (12) https://doi.org/10.1002/hlca.202000191
    67. Ferenc Béke, Ádám Mészáros, Ágnes Tóth, Bence Béla Botlik, Zoltán Novák. Vicinal difunctionalization of carbon–carbon double bond for the platform synthesis of trifluoroalkyl amines. Nature Communications 2020, 11 (1) https://doi.org/10.1038/s41467-020-19748-z
    68. Carlos Lázaro-Milla, Eduardo Busto, Imanol Burgos, Olalla Nieto Faza, Pedro Almendros. Gold-catalyzed reaction of alkynes with diazonium salts under photoirradiation revisited: New alkoxyarylation variant leading to enol ethers. Journal of Catalysis 2020, 391 , 48-55. https://doi.org/10.1016/j.jcat.2020.07.029
    69. Wei Ding, Chen Wang, Jie Ren Tan, Chang Chin Ho, Felix León, Felipe García, Naohiko Yoshikai. Site-selective aromatic C–H λ 3 -iodanation with a cyclic iodine( iii ) electrophile in solution and solid phases. Chemical Science 2020, 11 (28) , 7356-7361. https://doi.org/10.1039/D0SC02737E
    70. Jinkui Chai, Wei Ding, Junliang Wu, Naohiko Yoshikai. Fluorobenziodoxole−BF 3 Reagent for Iodo(III)etherification of Alkynes in Ethereal Solvent. Chemistry – An Asian Journal 2020, 15 (14) , 2166-2169. https://doi.org/10.1002/asia.202000653
    71. Jessica Neufeld, Constantin G Daniliuc, Ryan Gilmour. Fluorohydration of alkynes via I(I)/I(III) catalysis. Beilstein Journal of Organic Chemistry 2020, 16 , 1627-1635. https://doi.org/10.3762/bjoc.16.135