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
Platinum-Catalyzed Tandem Indole Annulation/Arylation for the Synthesis of Diindolylmethanes and Indolo[3,2-b]carbazoles
My Activity
    Letter

    Platinum-Catalyzed Tandem Indole Annulation/Arylation for the Synthesis of Diindolylmethanes and Indolo[3,2-b]carbazoles
    Click to copy article linkArticle link copied!

    View Author Information
    School of Pharmacy, University of Wisconsin, Madison, Wisconsin 53705, United States, and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States
    †School of Pharmacy.
    ‡Department of Chemistry.
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2013, 15, 16, 4162–4165
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol4018408
    Published August 5, 2013
    Copyright © 2013 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Various diindolylmethanes were prepared from propargylic ethers and substituted indoles via a platinum-catalyzed tandem indole annulation/arylation cascade. The resulting diindolylmethanes could be converted to natural product malassezin by formylation or indolo[3,2-b]carbazoles by cyclization.

    Copyright © 2013 American Chemical Society

    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. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    1H NMR, 13C NMR, IR, HRMS for starting materials and products. This material is available free of charge via the Internet at http://pubs.acs.org.

    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

    Click to copy section linkSection link copied!

    This article is cited by 47 publications.

    1. Kang Dong, Jia Li, Rui-Peng Li, Mingming Mao, Jian Liu, Xiaolei Wang, Shouchu Tang. One-Pot Sequential Synthesis of 3,3′- or 2,3′-Bis(indolyl)methanes by Using 1,3-Dithiane as the Methylene Source. The Journal of Organic Chemistry 2022, 87 (21) , 14930-14939. https://doi.org/10.1021/acs.joc.2c01844
    2. Jeff P. Costello, Eric M. Ferreira. Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O–H and N–H Additions. Organic Letters 2019, 21 (24) , 9934-9939. https://doi.org/10.1021/acs.orglett.9b03557
    3. Ferruh Lafzi, Haydar Kilic, Nurullah Saracoglu. Protocols for the Syntheses of 2,2′-Bis(indolyl)arylmethanes, 2-Benzylated Indoles, and 5,7-Dihydroindolo[2,3-b]carbazoles. The Journal of Organic Chemistry 2019, 84 (18) , 12120-12130. https://doi.org/10.1021/acs.joc.9b02124
    4. Jinhuan Dong, Dawei Zhang, Yang Men, Xueming Zhang, Zhongyan Hu, Xianxiu Xu. [1 + 2 + 3] Annulation as a General Access to Indolo[3,2-b]carbazoles: Synthesis of Malasseziazole C. Organic Letters 2019, 21 (1) , 166-169. https://doi.org/10.1021/acs.orglett.8b03646
    5. Tomasz Janosik, Agneta Rannug, Ulf Rannug, Niklas Wahlström, Johnny Slätt, Jan Bergman. Chemistry and Properties of Indolocarbazoles. Chemical Reviews 2018, 118 (18) , 9058-9128. https://doi.org/10.1021/acs.chemrev.8b00186
    6. Nobuharu Iwasawa, Shoya Watanabe, Akane Ario, Hideyuki Sogo. Re(I)-Catalyzed Hydropropargylation of Silyl Enol Ethers Utilizing Dynamic Interconversion of Vinylidene–Alkenylmetal Intermediates via 1,5-Hydride Transfer. Journal of the American Chemical Society 2018, 140 (25) , 7769-7772. https://doi.org/10.1021/jacs.8b02903
    7. Khoi Q. Huynh, Curtis A. Seizert, Tarik J. Ozumerzifon, Paul A. Allegretti, and Eric M. Ferreira . Platinum-Catalyzed α,β-Unsaturated Carbene Formation in the Formal Syntheses of Frondosin B and Liphagal. Organic Letters 2017, 19 (1) , 294-297. https://doi.org/10.1021/acs.orglett.6b03682
    8. Swastik Karmakar, Prasanta Das, Debjyoti Ray, Subhankar Ghosh, and Shital K. Chattopadhyay . Ag(I)-Catalyzed Domino Cyclization–Addition Sequence with Simultaneous Carbonyl and Alkyne Activation as a Route to 2,2′-Disubstituted Bisindolylarylmethanes. Organic Letters 2016, 18 (20) , 5200-5203. https://doi.org/10.1021/acs.orglett.6b02321
    9. Paul A. Allegretti, Khoi Huynh, Tarik J. Ozumerzifon, and Eric M. Ferreira . Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene. Organic Letters 2016, 18 (1) , 64-67. https://doi.org/10.1021/acs.orglett.5b03246
    10. Zhiyuan Chen, Xuegong Jia, Jiapian Huang, and Jianjun Yuan . Platinum-Catalyzed Tandem Cycloisomerization Reaction of Benzoendiynyl Esters: Regioselective Long-Range 1,5-Acyl Migration. The Journal of Organic Chemistry 2014, 79 (21) , 10674-10681. https://doi.org/10.1021/jo5020245
    11. Shivaji B. Markad and Narshinha P. Argade . Diversity Oriented Convergent Access for Collective Total Synthesis of Bioactive Multifunctional Carbazole Alkaloids: Synthesis of Carbazomycin A, Carbazomycin B, Hyellazole, Chlorohyellazole, and Clausenaline D. Organic Letters 2014, 16 (20) , 5470-5473. https://doi.org/10.1021/ol502721r
    12. Yongseok Kwon, Illan Kim, and Sanghee Kim . Platinum-Catalyzed Synthesis of Substituted Phenanthrenes from Biphenyl Propargyl Alcohols via a Carbene Intermediate. Organic Letters 2014, 16 (18) , 4936-4939. https://doi.org/10.1021/ol502465e
    13. Can Zhu and Shengming Ma . Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal Alkynes. Organic Letters 2014, 16 (6) , 1542-1545. https://doi.org/10.1021/ol500119r
    14. Paul A. Allegretti and Eric M. Ferreira . Vicinal Bisheterocyclizations of Alkynes via Nucleophilic Interception of a Catalytic Platinum Carbene. Journal of the American Chemical Society 2013, 135 (46) , 17266-17269. https://doi.org/10.1021/ja408957a
    15. Qingdong Hu, Chang Guo. Platinum/Copper Dual‐Catalyzed Asymmetric Vinylogous Addition Reactions for the Synthesis of Functionalized Indoles. Angewandte Chemie International Edition 2023, 62 (30) https://doi.org/10.1002/anie.202305638
    16. Qingdong Hu, Chang Guo. Platinum/Copper Dual‐Catalyzed Asymmetric Vinylogous Addition Reactions for the Synthesis of Functionalized Indoles. Angewandte Chemie 2023, 135 (30) https://doi.org/10.1002/ange.202305638
    17. Debayan Roy, Prabhakararao Tharra, Beeraiah Baire. An approach to functionalized carbazoles from Z -enoate propargylic alcohols. A unified total synthesis of N -Me-carazostatin, N -Me-carbazoquinocin C and N -Me-lipocarbazole A4. Chemical Communications 2022, 58 (73) , 10210-10213. https://doi.org/10.1039/D2CC03526J
    18. Shakir Ahamad, Shintu Mathew, Waqas A. Khan, Kishor Mohanan. Development of small-molecule PCSK9 inhibitors for the treatment of hypercholesterolemia. Drug Discovery Today 2022, 27 (5) , 1332-1349. https://doi.org/10.1016/j.drudis.2022.01.014
    19. Haohua Chen, Yuanyuan Li, Song Liu, Qin Xiong, Ruopeng Bai, Donghui Wei, Yu Lan. On the mechanism of homogeneous Pt-catalysis: A theoretical view. Coordination Chemistry Reviews 2021, 437 , 213863. https://doi.org/10.1016/j.ccr.2021.213863
    20. . Theoretical Study of Pt ‐ C atalysis. 2021, 257-287. https://doi.org/10.1002/9783527346028.ch6
    21. Xiao‐Yan Liu, Yun‐Lin Liu, Long Chen. Tandem Annulations of Propargylic Alcohols to Indole Derivatives. Advanced Synthesis & Catalysis 2020, 362 (23) , 5170-5195. https://doi.org/10.1002/adsc.202000930
    22. Joana F. Campos, Sabine Berteina-Raboin. Tandem Catalysis: Synthesis of Nitrogen-Containing Heterocycles. Catalysts 2020, 10 (6) , 631. https://doi.org/10.3390/catal10060631
    23. Hao Wu, Binkai Liu, Ka Yang, Gabrielle N. Winston-McPherson, Eric D. Leisten, Chad M. Vezina, William A. Ricke, Richard E. Peterson, Weiping Tang. Synthesis and biological evaluation of FICZ analogues as agonists of aryl hydrocarbon receptor. Bioorganic & Medicinal Chemistry Letters 2020, 30 (5) , 126959. https://doi.org/10.1016/j.bmcl.2020.126959
    24. José Sebastião Santos Neto, Gilson Zeni. Recent advances in the synthesis of indoles from alkynes and nitrogen sources. Organic Chemistry Frontiers 2020, 7 (1) , 155-210. https://doi.org/10.1039/C9QO01315F
    25. Cunyu Zhang, Katrina L. Creech, William J. Zuercher, Timothy M. Willson. Gram-scale synthesis of FICZ, a photoreactive endogenous ligand of the aryl hydrocarbon receptor. Scientific Reports 2019, 9 (1) https://doi.org/10.1038/s41598-019-46374-7
    26. Gabrielle N. Winston-McPherson, Haibo Xie, Ka Yang, Xiaoxun Li, Dongxu Shu, Weiping Tang. Discovery of 2,3′-diindolylmethanes as a novel class of PCSK9 modulators. Bioorganic & Medicinal Chemistry Letters 2019, 29 (16) , 2345-2348. https://doi.org/10.1016/j.bmcl.2019.06.014
    27. Wangze Song, Ming Li, Junnan He, Junhao Li, Kun Dong, Yubin Zheng. Copper-catalyzed tandem annulation/enol nucleophilic addition to access multisubstituted indoles. Organic & Biomolecular Chemistry 2019, 17 (10) , 2663-2669. https://doi.org/10.1039/C9OB00181F
    28. Sadhanendu Samanta, Alakananda Hajra. Ruthenium-catalyzed tandem annulation/arylation for the synthesis of unsymmetrical bis(heteroaryl)methanes. Organic & Biomolecular Chemistry 2018, 16 (37) , 8390-8394. https://doi.org/10.1039/C8OB01892H
    29. Lisa Cooper, José Miguel Alonso, Louise Eagling, Helen Newson, Sachini Herath, Christopher Thomson, Andrew Lister, Catherine Howsham, Brian Cox, María Paz Muñoz. Synthesis of a Novel Type of 2,3′‐BIMs via Platinum‐Catalysed Reaction of Indolylallenes with Indoles. Chemistry – A European Journal 2018, 24 (23) , 6105-6114. https://doi.org/10.1002/chem.201705417
    30. Tongxiang Cao, Kai Chen, Shifa Zhu. An efficient approach to generate aryl carbenes: gold-catalyzed sequential activation of 1,6-diynes. Organic Chemistry Frontiers 2017, 4 (3) , 450-454. https://doi.org/10.1039/C6QO00769D
    31. Tian‐Ren Li, Bei‐Yi Cheng, Ya‐Ni Wang, Mao‐Mao Zhang, Liang‐Qiu Lu, Wen‐Jing Xiao. A Copper‐Catalyzed Decarboxylative Amination/Hydroamination Sequence: Switchable Synthesis of Functionalized Indoles. Angewandte Chemie 2016, 128 (40) , 12610-12614. https://doi.org/10.1002/ange.201605900
    32. Tian‐Ren Li, Bei‐Yi Cheng, Ya‐Ni Wang, Mao‐Mao Zhang, Liang‐Qiu Lu, Wen‐Jing Xiao. A Copper‐Catalyzed Decarboxylative Amination/Hydroamination Sequence: Switchable Synthesis of Functionalized Indoles. Angewandte Chemie International Edition 2016, 55 (40) , 12422-12426. https://doi.org/10.1002/anie.201605900
    33. Xiaoxun Li, Haibo Xie, Xiaoning Fu, Ji‐tian Liu, Hao‐yuan Wang, Bao‐min Xi, Peng Liu, Xiufang Xu, Weiping Tang. Rhodium(I)‐Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles. Chemistry – A European Journal 2016, 22 (30) , 10410-10414. https://doi.org/10.1002/chem.201602088
    34. . Platinum‐Catalyzed Indole Ring Synthesis. 2016, 648-650. https://doi.org/10.1002/9781118695692.ch83
    35. Sinan Bayindir, Nurullah Saracoglu. A facile one-pot method to synthesise 2-alkylated indole and 2,2′-bis(indolyl)methane derivatives using ketones as electrophiles and their anion sensing ability. RSC Advances 2016, 6 (77) , 72959-72967. https://doi.org/10.1039/C6RA16192H
    36. James W. Herndon. The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2013. Coordination Chemistry Reviews 2015, 286 , 30-150. https://doi.org/10.1016/j.ccr.2014.09.021
    37. Minoru Ishikura, Takumi Abe, Tominari Choshi, Satoshi Hibino. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit. Natural Product Reports 2015, 32 (10) , 1389-1471. https://doi.org/10.1039/C5NP00032G
    38. Daisuke Sekine, Shota Okeda, Seijiro Hosokawa. Concise Synthesis of 6-Formylindolo[3,2- b ]carbazole (FICZ). Chemistry Letters 2014, 43 (12) , 1932-1934. https://doi.org/10.1246/cl.140843
    39. Gabrielle N. Winston-McPherson, Dongxu Shu, Weiping Tang. Synthesis and biological evaluation of 2,3′-diindolylmethanes as agonists of aryl hydrocarbon receptor. Bioorganic & Medicinal Chemistry Letters 2014, 24 (16) , 4023-4025. https://doi.org/10.1016/j.bmcl.2014.06.009
    40. Nuligonda Thirupathi, Yalla Kiran Kumar, Ruchir Kant, Maddi Sridhar Reddy. Selective 5‐ exo‐dig Cyclization of in Situ Synthesized N ‐Boc‐2‐aminophenyl Ethoxyethynyl Carbenols: Synthesis of Multifunctional Indoles and Their Derivatives. Advanced Synthesis & Catalysis 2014, 356 (8) , 1823-1834. https://doi.org/10.1002/adsc.201301002
    41. Dongxu Shu, Gabrielle N. Winston‐McPherson, Wangze Song, Weiping Tang. ChemInform Abstract: Platinum‐Catalyzed Tandem Indole Annulation/Arylation for the Synthesis of Diindolylmethanes and Indolo[3,2‐b]carbazoles.. ChemInform 2014, 45 (2) https://doi.org/10.1002/chin.201402108
    42. Gang Liu, Guangyang Xu, Jian Li, Dong Ding, Jiangtao Sun. Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: the direct synthesis of C2-functionalized indoles. Org. Biomol. Chem. 2014, 12 (9) , 1387-1390. https://doi.org/10.1039/C3OB42350F
    43. Hui Li, Xiaoxun Li, Hao-Yuan Wang, Gabrielle N. Winston-McPherson, Hao-miao Julie Geng, Ilia A. Guzei, Weiping Tang. Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols. Chem. Commun. 2014, 50 (82) , 12293-12296. https://doi.org/10.1039/C4CC05901H
    44. Amir Taheri, Changhui Liu, Bingbing Lai, Cheng Cheng, Xiaojuan Pan, Yanlong Gu. Brønsted acid ionic liquid catalyzed facile synthesis of 3-vinylindoles through direct C3 alkenylation of indoles with simple ketones. Green Chem. 2014, 16 (8) , 3715-3719. https://doi.org/10.1039/C4GC00840E
    45. Qingjiang Li, Xiao-Shui Peng, Henry N. C. Wong. Brønsted acid-catalyzed synthesis of carbazoles from 2-substituted indoles. Org. Chem. Front. 2014, 1 (10) , 1197-1200. https://doi.org/10.1039/C4QO00242C
    46. Jin-Feng Zou, Hu Wang, Li Li, Zheng Xu, Ke-Fang Yang, Li-Wen Xu. Fe-catalyzed cycloaddition of indoles and o-phthalaldehyde for the synthesis of benzo[b]carbazoles with TMSCl- or acid-responsive properties. RSC Adv. 2014, 4 (88) , 47272-47277. https://doi.org/10.1039/C4RA08012B
    47. Cheng Zhang, Lan-Xi Zhang, Yang Qiu, Biao Xu, Yu Zong, Qi-Xiang Guo. Highly efficient [3 + 2] reaction of 3-vinylindoles with 3-indolylmethanols by Brønsted-acid catalysis. RSC Advances 2014, 4 (14) , 6916. https://doi.org/10.1039/c3ra47056c

    Organic Letters

    Cite this: Org. Lett. 2013, 15, 16, 4162–4165
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol4018408
    Published August 5, 2013
    Copyright © 2013 American Chemical Society

    Article Views

    2487

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.