Rhodium(III)-Catalyzed Selective ortho-Olefinations of N-Acyl and N-Aroyl Sulfoximines by C-H Bond Activation

被引:93
作者
Parthasarathy, Kanniyappan [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
alkenes; CH bond activation; olefination; ortho-alkenylation; rhodium catalysis; CATALYZED OXIDATIVE ALKENYLATION; PD(II)-CATALYZED OLEFINATION; DIRECTING GROUP; HECK REACTION; ALKYNES; ALKENES; ARENES; FUNCTIONALIZATION; ANILIDES; CLEAVAGE;
D O I
10.1002/chem.201304925
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two new rhodium-catalyzed oxidative couplings between sulfoximine derivatives and alkenes by regioselective CH activation, affording ortho-olefinated (Heck-type) products, are reported. A synthetic application of the ortho-alkenylated products into the corresponding cyclic derivatives has been demonstrated, and a mechanistic rational for the rhodium catalysis is presented.
引用
收藏
页码:4896 / 4900
页数:5
相关论文
共 106 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water [J].
Ackermann, Lutz ;
Wang, Lianhui ;
Wolfram, Ratnakancana ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :728-731
[3]   Ruthenium-Catalyzed Oxidative C-H Bond Alkenylations in Water: Expedient Synthesis of Annulated Lactones [J].
Ackermann, Lutz ;
Pospech, Jola .
ORGANIC LETTERS, 2011, 13 (16) :4153-4155
[4]  
[Anonymous], SYNTHESIS
[5]  
[Anonymous], 2009, ANGEW CHEM INT ED, V48, P5094
[6]  
[Anonymous], ORGANOSULFUR CHEM AS
[7]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P1064
[8]  
[Anonymous], ANGEW CHEM INT ED
[9]  
[Anonymous], ANGEW CHEM INT ED
[10]  
[Anonymous], ANGEW CHEM INT ED