Rhodium(I)-Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion

被引：64
|
作者：
Xia, Ying [1 ,2 ]
Feng, Sheng [1 ,2 ]
Liu, Zhen [1 ,2 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ,3 ]
机构：
[1] Peking Univ, Coll Chem, BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 27期
关键词：
carbenes; cross-couplings; diazo compounds; migratory insertion; quaternary carbon center; NONACTIVATED ALKYL-HALIDES; CROSS-COUPLING REACTIONS; ALPHA-DIAZOCARBONYL COMPOUNDS; C-C BOND; GRIGNARD-REAGENTS; SONOGASHIRA REACTIONS; N-TOSYLHYDRAZONES; C(SP(3))-H BONDS; METAL CARBENE; ALKYNYLATION;
D O I：
10.1002/anie.201503140
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Rh-I-catalyzed three-component reaction of tert-propargyl alcohol, diazoester, and alkyl halide has been developed. This reaction can be considered as a carbene-involving sequential alkyl and alkynyl coupling, in which C(sp)C(sp(3)) and C(sp(3))C(sp(3)) bonds are built successively on the carbenic carbon atom. The Rh-I-carbene migratory insertion of an alkynyl moiety and subsequent alkylation are proposed to account for the two separate CC bond formations. This reaction provides an efficient and tunable method for the construction of all-carbon quaternary center.
引用
收藏
页码：7891 / 7894
页数：4
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