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!

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.

Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Geminal alkylation: substitutions of allyl sulfones. Regiocontrol via molybdenum catalysis

Cite this: J. Org. Chem. 1990, 55, 4, 1127–1129
Publication Date (Print):February 1, 1990
    ACS Legacy Archive

    Article Views





    Other access options
    Supporting Info (1)»

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    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.


    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

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at

    Cited By

    This article is cited by 54 publications.

    1. Wei-Dong Lu, Yu Zheng, Zhi-Peng Zhang, Hong-Bin Chen, Kai Chen, Hao-Yue Xiang, Hua Yang. Visible-Light-Induced, Palladium-Mediated Desaturation/Sulfonation Cascade To Access 4-Sulfonyltetrahydropyridine Scaffolds. Organic Letters 2023, 25 (32) , 6077-6081.
    2. Masakazu Nambo, Yuuki Maekawa, Cathleen M. Crudden. Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis. ACS Catalysis 2022, 12 (5) , 3013-3032.
    3. Zhen Luo, Zheng-Qiang Liu, Ting-Ting Yang, Xin Zhuang, Chuan-Ming Hong, Fei-Fei Zou, Zhi-Yong Xue, Qing-Hua Li, Tang-Lin Liu. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-Assisted Catalyst-Free Sulfonation of Allylic Alcohols with Sulfinyl Amides. Organic Letters 2022, 24 (2) , 741-745.
    4. Suman Dana, Chandan Kumar Giri, Mahiuddin Baidya. Ruthenium(II)-Catalyzed Regioselective C–H Olefination of Aromatic Ketones and Amides with Allyl Sulfones. Organic Letters 2021, 23 (17) , 6855-6860.
    5. Yaoyao Xu, Muhammad Salman, Shahid Khan, Junjie Zhang, Ajmal Khan. Tungsten-Catalyzed Allylic Substitution with a Heteroatom Nucleophile: Reaction Development and Synthetic Applications. The Journal of Organic Chemistry 2020, 85 (17) , 11501-11510.
    6. Xue Lei, Lei Zheng, Chuanxin Zhang, Xiaodong Shi, and Yunfeng Chen . Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation. The Journal of Organic Chemistry 2018, 83 (4) , 1772-1778.
    7. Markus Jegelka and Bernd Plietker. Selective C−S Bond Formation via Fe-Catalyzed Allylic Substitution. Organic Letters 2009, 11 (15) , 3462-3465.
    8. Ahmad El-Awa, Mohammad N. Noshi, Xavier Mollat du Jourdin and Philip L. Fuchs. Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety. Chemical Reviews 2009, 109 (6) , 2315-2349.
    9. Mohammad N. Noshi,, Ahmad El-Awa, and, Philip L. Fuchs. Second-Generation Synthesis of syn- and anti-Cycloheptadienylsulfone Polyketide Stereodiads. The Journal of Organic Chemistry 2008, 73 (8) , 3274-3277.
    10. Vicenç Branchadell,, Marcial Moreno-Mañas, and, Roser Pleixats. Theoretical Study on the Regioselectivity of Nucleophilic Attack in Silyl-Substituted (Diphosphino)(η3-allyl)palladium Cations. Organometallics 2002, 21 (12) , 2407-2412.
    11. Vicenç Branchadell,, Marcial Moreno-Mañas,, Francesca Pajuelo, and, Roser Pleixats. Density Functional Study on the Regioselectivity of Nucleophilic Attack in 1,3-Disubstituted (Diphosphino)(η3-allyl)palladium Cations. Organometallics 1999, 18 (24) , 4934-4941.
    12. Ryo Takeuchi and, Mikihiro Kashio. Iridium Complex-Catalyzed Allylic Alkylation of Allylic Esters and Allylic Alcohols:  Unique Regio- and Stereoselectivity. Journal of the American Chemical Society 1998, 120 (34) , 8647-8655.
    13. Magnus P. T. Sjögren,, Håkan Frisell, and, Björn Åkermark, , Per-Ola Norrby, , Lars Eriksson, , Aldo Vitagliano. Molybdenum-Catalyzed Allylic Substitution. Influence of 1,10-Phenanthroline Ligands on Reactivity and Selectivity. Organometallics 1997, 16 (5) , 942-950.
    14. Marcial Moreno-Mañas,, Francesca Pajuelo,, Teodor Parella, and, Roser Pleixats. Preparation and NMR Spectroscopy of (1,2-Bis(diphenylphosphino)ethane)(η3-1,3-diarylallyl)- palladium Tetrafluoroborates. Correlation of Chemical Shifts with Hammett Substituent Constants and with the Regioselectivity of Nucleophilic Attack. Organometallics 1997, 16 (2) , 205-209.
    15. Barry M. Trost, Zhiwei Jiao, Hadi Gholami. Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles. Chemical Science 2021, 12 (31) , 10532-10537.
    16. Muhammad Salman, Yaoyao Xu, Shahid Khan, Junjie Zhang, Ajmal Khan. Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications. Chemical Science 2020, 11 (21) , 5481-5486.
    17. Koji Takizawa, Tomoyuki Sekino, Shunta Sato, Tatsuhiko Yoshino, Masahiro Kojima, Shigeki Matsunaga. Cobalt‐Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis. Angewandte Chemie 2019, 131 (27) , 9297-9301.
    18. Koji Takizawa, Tomoyuki Sekino, Shunta Sato, Tatsuhiko Yoshino, Masahiro Kojima, Shigeki Matsunaga. Cobalt‐Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis. Angewandte Chemie International Edition 2019, 58 (27) , 9199-9203.
    19. Chunsheng Li, Jianxiao Li, Chaowei Tan, Wanqing Wu, Huanfeng Jiang. DDQ-mediated regioselective C–S bond formation: efficient access to allylic sulfides. Organic Chemistry Frontiers 2018, 5 (21) , 3158-3162.
    20. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Alkylation and Acylation of Aldehydes, Ketones, and Their Derivatives. 2018, 1-145.
    21. Richard C. Larock, Tuanli Yao. Formation of Nitriles, Carboxylic Acids, and Derivatives by Alkylation, Acylation, and Substitution. 2018, 1-139.
    22. Manijeh Nematpour, Elahe Abedi. An efficient synthesis of novel sulfonyl[3.3.3]heteropropellanes from sulfonylacetamidines and ninhydrin-malononitrile adduct. Journal of Sulfur Chemistry 2017, 38 (3) , 229-235.
    23. Barry M. Trost, Walter H. Chan, Sushant Malhotra. Development of the Regiodivergent Asymmetric Prenylation of 3‐Substituted Oxindoles. Chemistry – A European Journal 2017, 23 (18) , 4405-4414.
    24. Manijeh Nematpour, Samira Rasouli Koohi, Elahe Abedi, Mahbob Lotfi. A Green, One-Pot Formation of Imidazolone and Pyrimidinone Derivatives Containing a Sulfonyl Group. Journal of Chemical Research 2016, 40 (11) , 652-654.
    25. Richard K. Haynes, Simone C. Vonwiller, Vikas Sikervar. Allyl Phenyl Sulfone. 2016, 1-6.
    26. Anton Bayer, Uli Kazmaier. Cross‐Coupling Reactions via sπ‐Allylmetal Intermediates. 2014, 925-994.
    27. R. Fernández de la Pradilla, A. Viso. 3.03 Alkylation of α-Sulfur-Containing Carbanions. 2014, 157-208.
    28. Takeshi Hata, Takuya Nakada, Yun Taek Oh, Naoki Hirone, Hirokazu Urabe. Iron‐Catalyzed Regio‐ and Stereoselective Conjugate Addition of Aryl‐Grignard Reagents to α,β,γ,δ‐Unsaturated Sulfones and its Synthetic Application. Advanced Synthesis & Catalysis 2013, 355 (9) , 1736-1740.
    29. Erich F. Altenhofer, Michael Harmata. Generation and alkylation of 2-boryl allylic sulfone anions. Chemical Communications 2013, 49 (23) , 2365.
    30. Issa Yavari, Manijeh Nematpour. Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates. Molecular Diversity 2012, 16 (4) , 651-657.
    31. Markus Jegelka, Bernd Plietker. α‐Sulfonyl Succinimides: Versatile Sulfinate Donors in Fe‐Catalyzed, Salt‐Free, Neutral Allylic Substitution. Chemistry – A European Journal 2011, 17 (37) , 10417-10430.
    32. John F. Hartwig, Mark J. Pouy. Iridium-Catalyzed Allylic Substitution. 2011, 169-208.
    33. Diego A. Alonso, Carmen N Ájera. Desulfonylation Reactions. 2009, 367-656.
    34. Nicolas Charrier, Samir Z. Zard. Radical Allylation with α‐Branched Allyl Sulfones. Angewandte Chemie 2008, 120 (49) , 9585-9588.
    35. Nicolas Charrier, Samir Z. Zard. Radical Allylation with α‐Branched Allyl Sulfones. Angewandte Chemie International Edition 2008, 47 (49) , 9443-9446.
    36. Daniel A. Singleton, Chad F. Christian. Isotope effects and the mechanism of palladium-catalyzed allylic alkylation. Tetrahedron Letters 2005, 46 (10) , 1631-1634.
    37. Ji Won Pack, Young-Jae Hur, Hwayong Kim, Youn-Woo Lee. Cyclopolymerization of dimethyl dipropargylmalonate in supercritical carbon dioxide to give a highly regular polyene containing predominantly five-membered rings. Chemical Communications 2005, 99 (41) , 5208.
    38. Marion G. Götz, Conor R. Caffrey, Elizabeth Hansell, James H. McKerrow, James C. Powers. Peptidyl allyl sulfones: a new class of inhibitors for clan CA cysteine proteases. Bioorganic & Medicinal Chemistry 2004, 12 (19) , 5203-5211.
    39. Uli Kazmaier, Matthias Pohlman. Cross‐Coupling Reactions via π‐Allylmetal Intermediates. 2004, 531-583.
    40. Jitender M. Khurana, Sushma Chauhan, Arpita Agrawal. MOLYBDENUM IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 2004, 36 (3) , 201-276.
    41. Hans‐Joachim Gais, Thomas Jagusch, Nicole Spalthoff, Frank Gerhards, Michael Frank, Gerhard Raabe. Highly Selective Palladium Catalyzed Kinetic Resolution and Enantioselective Substitution of Racemic Allylic Carbonates with Sulfur Nucleophiles: Asymmetric Synthesis of Allylic Sulfides, Allylic Sulfones, and Allylic Alcohols. Chemistry – A European Journal 2003, 9 (17) , 4202-4221.
    42. Takako Muraoka, Isamu Matsuda, Kenji Itoh. Rhodium-catalyzed substitution of allylic carbonates with enoxysilanes. Tetrahedron Letters 2000, 41 (45) , 8807-8811.
    43. Carmen Nájera, Miguel Yus. Desulfonylation reactions: Recent developments. Tetrahedron 1999, 55 (35) , 10547-10658.
    44. Akihiro Orita, Akihiro Watanabe, Hiroshi Tsuchiya, Junzo Otera. Integrated chemical process. Construction of highly substituted allylic moieties from allylic sulfones in one-pot. Tetrahedron 1999, 55 (10) , 2889-2898.
    45. Francisco Caturla, Carmen Nájera. Studies on the reactivity of methyl γ-tosylcrotonoate as ambident reagent in organic synthesis. Tetrahedron 1996, 52 (48) , 15243-15256.
    46. . Preparation of Esters. 1995, 166-183.
    47. Timothy N. Birkinshaw. One or More CC Bond(s) Formed by Substitution: Substitution of Chalcogen. 1995, 171-247.
    48. . References to Volume 1. 1995, 1147-1316.
    49. Peter J. Harrington. Transition Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack. 1995, 797-904.
    50. Diego A. Alonso, Carmen Nájera, José M. Sansano. Tosylated lithium 2-(lithiomethyl)-2-propen-1-olate: a γ-alkoxide allyl sulfone anion in organic synthesis. Tetrahedron 1994, 50 (22) , 6603-6620.
    51. . Desulphonylation. 1993, 334-372.
    52. Louis S. Hegedus. Transition metals in organic synthesis annual survey covering the year 1990. Journal of Organometallic Chemistry 1992, 422 (1-3) , 301-681.
    53. B. M. TROST, C. A. MERLIC. ChemInform Abstract: Geminal Alkylation: Substitutions of Allyl Sulfones. Regiocontrol via Molybdenum Catalysis.. ChemInform 1990, 21 (30)
    54. Andreas Stolle, Jacques Salaün, Armin de Meijere. Palladium(0) catalyzed substitution reactions of cyclopropyl group containing allylic esters. Tetrahedron Letters 1990, 31 (32) , 4593-4596.