Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes

被引：69

作者：

Chen, Xiao Yun ^{[1
]}

Wang, Long ^{[1
]}

Frings, Marcus ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 14期

关键词：

ASYMMETRIC-SYNTHESIS; OXIDATIVE AMIDATION; TERMINAL ALKYNES; YNAMIDES; BROMIDES;

D O I：

10.1021/ol5016898

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Alkynylated sulfoximines have been obtained by copper-catalyzed cross-coupling reactions starting from NH-sulfoximines and bromoacetylenes in moderate to good yields. The reaction conditions are mild, and the substrate scope is wide.

引用

页码：3796 / 3799

页数：4

共 45 条

[1] Synthesis of α-Keto-Imides via Oxidation of Ynamides [J].

Al-Rashid, Ziyad F. ;

Johnson, Whitney L. ;

Hsung, Richard P. ;

Wei, Yonggang ;

Yao, Pei-Yuan ;

Liu, Renhei ;

Zhao, Kang .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8780-8784

[2] Elusive ethynyl azides: trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes [J].

Banert, Klaus ;

Hagedorn, Manfred ;

Wutke, Jens ;

Ecorchard, Petra ;

Schaarschmidt, Dieter ;

Lang, Heinrich .

CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4058-4060

[3] ACTION OF NITROGEN TRICHLORIDE ON CERTAIN PROTEINS .1. ISOLATION AND IDENTIFICATION OF THE TOXIC FACTOR [J].

BENTLEY, HR ;

MCDERMOTT, EE ;

MORAN, T ;

PACE, J ;

WHITEHEAD, JK .

PROCEEDINGS OF THE ROYAL SOCIETY SERIES B-BIOLOGICAL SCIENCES, 1950, 137 (888) :402-+

[4] TOXIC FACTOR FROM AGENIZED PROTEINS - METHIONINE AS THE ESSENTIAL REACTANT [J].

BENTLEY, HR ;

MCDERMOTT, EE ;

PACE, J ;

WHITEHEAD, JK ;

MORAN, T .

NATURE, 1950, 165 (4187) :150-151

[5] Fluorinated sulfoximines: syntheses, properties and applications [J].

Bizet, Vincent ;

Kowalczyk, Rafal ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2426-2438

[6]

Bolm C., 2007, ASYMMETRIC SYNTHESIS, P149, DOI DOI 10.1002/9783527610648.CH2A

[7] Cationic rhodium(I)-diolefin complexes containing an optically active C2-symmetric bis(sulfoximine) ligand: Synthesis and catalytic activity [J].

Cadierno, Victorio ;

Diez, Josefina ;

Garcia-Garrido, Sergio E. ;

Gimeno, Jose ;

Pizzano, Antonio .

POLYHEDRON, 2010, 29 (18) :3380-3386

[8] Ynamides: A Modern Functional Group for the New Millennium [J].

DeKorver, Kyle A. ;

Li, Hongyan ;

Lohse, Andrew G. ;

Hayashi, Ryuji ;

Lu, Zhenjie ;

Zhang, Yu ;

Hsung, Richard P. .

CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106

[9] Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].

Dunetz, JR ;

Danheiser, RL .

ORGANIC LETTERS, 2003, 5 (21) :4011-4014

[10] General Amination Reactions for the Synthesis of Ynamides [J].

Evano, Gwilherm ;

Jouvin, Kevin ;

Coste, Alexis .

SYNTHESIS-STUTTGART, 2013, 45 (01) :17-26

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