Rhodium(I)-Catalyzed C-C Bond Activation of Siloxyvinylcyclopropanes with Diazoesters

被引:26
|
作者
Feng, Sheng [1 ,2 ]
Mo, Fanyang [1 ,2 ,3 ]
Xia, Ying [1 ,2 ]
Liu, Zhenxing [1 ,2 ]
Liu, Zhen [1 ,2 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ]
机构
[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
[3] Peking Univ, Coll Engn, Dept Energy & Resources Engn, Beijing 100871, Peoples R China
关键词
C-C activation; carbenes; diazo compounds; rhodium; small ring systems; INTRAMOLECULAR 3+2 CYCLOADDITION; CATALYZED 5+2+1 CYCLOADDITION; NATURAL-PRODUCT SYNTHESIS; DIELS-ALDER REACTION; ENE-VINYLCYCLOPROPANES; METAL CARBENE; ALKYNES; TOSYLHYDRAZONES; INSERTION; 1ST;
D O I
10.1002/anie.201609642
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The rhodium(I)-catalyzed C-C bond activation reaction of siloxyvinylcyclopropanes with diazoesters demonstrates a novel mode of C-C bond cleavage of siloxyvinvylcyclopanes. The alkene products were obtained as single E-configured isomers in good yields. A sigma,(3)-allyl rhodium complex, which has been previously proposed as the key intermediate in rhodium(I)-catalyzed cycloaddition of vinylcyclopropanes, has been isolated and characterized by X-ray crystallography.
引用
收藏
页码:15401 / 15405
页数:5
相关论文
共 50 条
  • [41] Rhodium Catalyzed Regioselective C-H Allylation of Simple Arenes via C-C Bond Activation of Gem-difluorinated Cyclopropanes
    Jiang, Zhong-Tao
    Huang, Jiangkun
    Zeng, Yaxin
    Hu, Fangdong
    Xia, Ying
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (19) : 10626 - 10631
  • [42] FLUO 22-Niobium-catalyzed C-F bond activation and C-C bond formation
    Akiyama, Takahiko
    Fuchibe, Kohei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 951 - 951
  • [43] Selective C-C vs C-H bond activation by rhodium(I) PCP pincer complexes. A computational study
    Sundermann, Andreas
    Uzan, Olivier
    Milstein, David
    Martin, Jan M.L.
    1600, ACS, Washington, DC, USA (122):
  • [44] Selective C-C vs C-H bond activation by rhodium(I) PCP pincer complexes. A computational study
    Sundermann, A
    Uzan, O
    Milstein, D
    Martin, JML
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) : 7095 - 7104
  • [45] Rhodium-catalyzed C-C coupling reactions via double C-H activation
    Li, Shuai-Shuai
    Qin, Liu
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) : 4554 - 4570
  • [46] Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water
    Xing, D
    Guan, BT
    Cai, GX
    Fang, Z
    Yang, LP
    Shi, ZJ
    ORGANIC LETTERS, 2006, 8 (04) : 693 - 696
  • [47] Rhodium(III)-Catalyzed C-C Coupling between Arenes and Aziridines by C-H Activation
    Li, Xingwei
    Yu, Songjie
    Wang, Fen
    Wan, Boshun
    Yu, Xinzhang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (09) : 2577 - 2580
  • [48] Ruthenium-catalyzed C-H activation and C-C bond formation.
    Gunnoe, TB
    Lail, M
    Arrowood, BN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U58 - U58
  • [49] Gold(I)-Catalyzed Tandem C-H and C-C Activation (Cleavage)
    Jiang, Min
    Liu, Le-Ping
    Shi, Min
    Li, Yuxue
    ORGANIC LETTERS, 2010, 12 (01) : 116 - 119
  • [50] Rhodium-Catalyzed Hiyama Coupling Reaction of Unstrained Ketones via C-C Bond Cleavage
    Jiang, Cheng
    Wu, Wen-Qiang
    Lu, Hong
    Yu, Tian-Yang
    Xu, Wen-Hua
    Wei, Hao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1358 - 1362