TBAF-Mediated Reactions of 1,1-Dibromo-1-alkenes with Thiols and Amines and Regioselective Synthesis of 1,2-Heterodisubstituted Alkenes

被引：51

作者：

Xu, Hui ^{[1
]}

Gu, Shaojin ^{[1
]}

Chen, Wanzhi ^{[1
]}

Li, Dacheng ^{[2
]}

Dou, Jianmin ^{[2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 08期

关键词：

CATALYZED ALKYNE HYDROTHIOLATION; INTRAMOLECULAR HYDROAMINATION; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; COUPLING REACTIONS; ADDITION-REACTION; INTERNAL ALKYNES; ARYL ALDEHYDES; VINYL SULFIDES; PALLADIUM;

D O I：

10.1021/jo2000176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of trisubstituted alkenes including 1,2-heterodisubstituted alkenes has been described. Reactions of thiols and amines with 1,1-dibromo-1-alkenes in the presence of TBAF center dot 3H(2)O afford (Z)-2-bromovinyl sulfides and (Z)-2-bromovinyl amines regio- and stereoselectively. The reaction proceeds under catalyst-free conditions with high efficiency. The coupling reactions of the obtained products bearing bromine atoms with phenylacetylene and phenylboronic acid gave trisubstituted alkenes in good to excellent yields. Cross-coupling with various N, O, S, and P nucleophiles selectively generated 1,2-N,O, 1,2-N,S, 1,2-S,P, 1,2-S,S, and 1,2-S,O heterodisubstituted alkenes.

引用

页码：2448 / 2458

页数：11

共 78 条

[1] Addition reaction of dialkyl disulfides to terminal alkynes catalyzed by a rhodium complex and trifluoromethanesulfonic acid [J].

Arisawa, M ;

Yamaguchi, M .

ORGANIC LETTERS, 2001, 3 (05) :763-764

[2] Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles [J].

Arthuis, Martin ;

Pontikis, Renee ;

Florent, Jean-Claude .

ORGANIC LETTERS, 2009, 11 (20) :4608-4611

[3] Addition reactions of E-E and E-H bonds to triple bond of alkynes catalyzed by Pd, Pt, and Ni complexes (E=S, Se) [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

PURE AND APPLIED CHEMISTRY, 2007, 79 (06) :1041-1056

[4] 1,1-Dibromo-1-alkenes as Valuable Partners in the Copper-Catalyzed Direct Alkynylation of Azoles [J].

Berciano, Beatriz Pacheco ;

Lebrequier, Sabrina ;

Besselievre, Francois ;

Piguel, Sandrine .

ORGANIC LETTERS, 2010, 12 (18) :4038-4041

[5] TOTAL SYNTHESIS OF (+)-LAURENCIN - USE OF ACETAL-VINYL SULFIDE CYCLIZATIONS FOR FORMING HIGHLY FUNCTIONALIZED 8-MEMBERED CYCLIC ETHERS [J].

BRATZ, M ;

BULLOCK, WH ;

OVERMAN, LE ;

TAKEMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (22) :5958-5966

[6] Inter- and Intramolecular Hydroamination with a Uranium Dialkyl Precursor [J].

Broderick, Erin M. ;

Gutzwiller, Nathaniel P. ;

Diaconescu, Paula L. .

ORGANOMETALLICS, 2010, 29 (15) :3242-3251

[7] A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity [J].

Bryan, Christopher S. ;

Lautens, Mark .

ORGANIC LETTERS, 2010, 12 (12) :2754-2757

[8] Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C-S Coupling [J].

Bryan, Christopher S. ;

Braunger, Julia A. ;

Lautens, Mark .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :7064-7068

[9] Late transition metal catalyzed intramolecular hydroamination: The effect of ligand and substrate structure [J].

Burling, Suzanne ;

Field, Leslie D. ;

Messerle, Barbara A. ;

Rumble, Sarah L. .

ORGANOMETALLICS, 2007, 26 (17) :4335-4343

[10] Rhodium-catalyzed alkyne hydrothiolation with aromatic and aliphatic thiols [J].

Cao, CS ;

Fraser, LR ;

Love, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17614-17615

← 1 2 3 4 5 6 7 8 →