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

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 33期

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

页码：4347 / 4350

页数：4

共 74 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

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 [J].

Behrends, Malte ;

Savmarker, Jonas ;

Sjoberg, Per J. R. ;

Larhed, Mats .

ACS CATALYSIS, 2011, 1 (11) :1455-1459

[5] Decarboxylative Ketone Aldol Reactions: Development and Mechanistic Evaluation under Metal-Free Conditions [J].

Blaquiere, Nicole ;

Shore, Daniel G. ;

Rousseaux, Sophie ;

Fagnou, Keith .

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 [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A ;

Parisi, LM ;

Bernini, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614

[7] Palladium-catalyzed desulfitative C-H arylation of azoles with sodium sulfinates [J].

Chen, Ru ;

Liu, Saiwen ;

Liu, Xinhua ;

Yang, Luo ;

Deng, Guo-Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) :7675-7679

[8] The First Effective Procedure for the Direct Esterification and Thiolysis of Sulfinic Acids [J].

Drabowicz, Jozef ;

Kwiatkowska, Malgorzata ;

Kielbasinski, Piotr .

SYNTHESIS-STUTTGART, 2008, (22) :3563-3564

[9] Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].

Dubbaka, SR ;

Vogel, P .

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 [J].

Duursma, A ;

Hoen, R ;

Schuppan, J ;

Hulst, R ;

Minnaard, AJ ;

Feringa, BL .

ORGANIC LETTERS, 2003, 5 (17) :3111-3113

← 1 2 3 4 5 6 7 8 →