Palladium-catalyzed desulfitative addition of sodium sulfinates with α,β-unsaturated carbonyl compounds

被引:37
作者
Chen, Wen [1 ]
Zhou, Xianya [1 ]
Xiao, Fuhong [1 ]
Luo, Jiaying [1 ]
Deng, Guo-Jun [1 ]
机构
[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Coll Chem, Xiangtan 411105, Peoples R China
基金
中国国家自然科学基金;
关键词
Addition; Desulfination; Palladium; Sulfinic acids; BOND-FORMING REACTIONS; HECK-TYPE REACTION; DIRECT ESI-MS; CONJUGATE ADDITION; ARYLBORONIC ACIDS; ARYL KETONES; ASYMMETRIC 1,4-ADDITION; COUPLING REACTION; BENZOIC-ACIDS; RHODIUM;
D O I
10.1016/j.tetlet.2012.06.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed desulfitative conjugate addition of sodium sulfinates with alpha,beta-unsaturated carbonyl compounds is described. The reaction showed very good selectivity and tolerated a wide range of functionalities under an atmosphere of argon. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4347 / 4350
页数:4
相关论文
共 74 条
  • [1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions
    Alexakis, A.
    Backvall, J. E.
    Krause, N.
    Pamies, O.
    Dieguez, M.
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 2796 - 2823
  • [2] Alexakis A., 1998, TRANSITION METALS OR, V4
  • [3] [Anonymous], 2000, OFFICIAL J EUROPEA L, V327, P73
  • [4] Microwave-Assisted Palladium(II)-Catalyzed Synthesis of Aryl Ketones from Aryl Sulfinates and Direct ESI-MS Studies Thereof
    Behrends, Malte
    Savmarker, Jonas
    Sjoberg, Per J. R.
    Larhed, Mats
    [J]. ACS CATALYSIS, 2011, 1 (11): : 1455 - 1459
  • [5] Decarboxylative Ketone Aldol Reactions: Development and Mechanistic Evaluation under Metal-Free Conditions
    Blaquiere, Nicole
    Shore, Daniel G.
    Rousseaux, Sophie
    Fagnou, Keith
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) : 6190 - 6198
  • [6] Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts
    Cacchi, S
    Fabrizi, G
    Goggiamani, A
    Parisi, LM
    Bernini, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) : 5608 - 5614
  • [7] Palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates
    Chen, Ru
    Liu, Saiwen
    Liu, Xinhua
    Yang, Luo
    Deng, Guo-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) : 7675 - 7679
  • [8] The First Effective Procedure for the Direct Esterification and Thiolysis of Sulfinic Acids
    Drabowicz, Jozef
    Kwiatkowska, Malgorzata
    Kielbasinski, Piotr
    [J]. SYNTHESIS-STUTTGART, 2008, (22): : 3563 - 3564
  • [9] Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions
    Dubbaka, SR
    Vogel, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) : 7674 - 7684
  • [10] First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach
    Duursma, A
    Hoen, R
    Schuppan, J
    Hulst, R
    Minnaard, AJ
    Feringa, BL
    [J]. ORGANIC LETTERS, 2003, 5 (17) : 3111 - 3113