Formal Carbene Insertion into C-C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters

被引：179
|
作者：
Xia, Ying [1 ]
Liu, Zhenxing [1 ]
Liu, Zhen [1 ]
Ge, Rui [1 ]
Ye, Fei [1 ]
Hossain, Mohammad [1 ]
Zhang, Yan [1 ]
Wang, Jianbo [1 ]
机构：
[1] Peking Univ, Coll Chem, Minist Educ, Beijing Natl Lab Mol Sci,Key Lab Bioorgan Chem &, Beijing 100871, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 08期
关键词：
ALPHA-DIAZOCARBONYL COMPOUNDS; CATALYZED CARBON-CARBON; DIAZO-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; SITE-SELECTIVITY; METAL CARBENE; ALKYNES; ACTIVATION; CONSTRUCTION; ARYL;
D O I：
10.1021/ja500118w
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Rh(I)-catalyzed formal carbene insertion into C-C bond of benzocyclobutenols has been realized by employing diazoesters as carbene precursors. The product indanol derivatives were obtained in good yields and in diastereoselective manner under mild reaction conditions. All-carbon quaternary center is constructed at the carbenic carbon. This catalytic reaction involves selective cleavage of C-C bond, Rh(I) carbene insertion, and intramolecular aldol reaction.
引用
收藏
页码：3013 / 3015
页数：3
相关论文
共 50 条
  • [1] Rh(I)-Catalyzed Insertion of Allenes into C-C Bonds of Benzocyclobutenols
    Zhao, Chunliang
    Liu, Li-Chuan
    Wang, Jing
    Jiang, Chenran
    Zhang, Qing-Wei
    He, Wei
    ORGANIC LETTERS, 2016, 18 (02) : 328 - 331
  • [2] Rhodium(I)-Catalyzed C-C Bond Activation of Siloxyvinylcyclopropanes with Diazoesters
    Feng, Sheng
    Mo, Fanyang
    Xia, Ying
    Liu, Zhenxing
    Liu, Zhen
    Zhang, Yan
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) : 15401 - 15405
  • [3] Gold-Catalyzed Formal C-C Bond Insertion Reaction of 2-Aryl-2-diazoesters with 1,3-Diketones
    Ren, Yuan-Yuan
    Chen, Mo
    Li, Ke
    Zhu, Shou-Fei
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (18) : 2606 - 2610
  • [4] Skeleton Reorganization of Substituted Benzocyclobutenols through Rh-Catalyzed C-C Bond Cleavage Manipulated by Hydrogen Transfer
    Dai, Ya-Mei
    Liu, Min
    Zeng, Qin-Qiong
    Li, Xiaoting
    Wang, Bi-Qin
    Hu, Ping
    Zhao, Ke-Qing
    Song, Feijie
    Shi, Zhang-Jie
    ORGANIC LETTERS, 2021, 23 (19) : 7597 - 7602
  • [5] A Rh(II)- or Ag(I)-Catalyzed Formal C-O Bond Insertion of Cyclic Hemiaminal with Aryl Diazoacetate
    Xu, Cong
    Liu, Xiangrong
    Xie, Xiongda
    Deng, Lin
    Xu, Xinfang
    Chan, Albert S. C.
    Hu, Wenhao
    SYNLETT, 2021, 32 (19) : 1957 - 1962
  • [6] Copper(I)-Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring-Opening C-C Bond Formations
    Zhang, Hang
    Wu, Guojiao
    Yi, Heng
    Sun, Tong
    Wang, Bo
    Zhang, Yan
    Dong, Guangbin
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 3945 - 3950
  • [7] Asymmetric formal C-C bond insertion into aldehydes via copper-catalyzed diyne cyclization
    Li, Cui-Ting
    Qi, Lin-Jun
    Liu, Li-Gao
    Ge, Chang
    Lu, Xin
    Ye, Long-Wu
    Zhou, Bo
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [8] Formal Carbene C-H Bond Insertion in the Cu(I)-Catalyzed Reaction of Bis(trimethylsilyl)diazomethane with Benzoxazoles and Oxazoles
    Wang, Shuai
    Xu, Shuai
    Yang, Cheng
    Sun, Hanli
    Wang, Jianbo
    ORGANIC LETTERS, 2019, 21 (06) : 1809 - 1812
  • [9] Regiospecific Synthesis of Benzoxepines through Pd-Catalyzed Carbene Migratory Insertion and C-C Bond Cleavage
    Xie, Yang
    Zhang, Ping
    Zhou, Lei
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05) : 2128 - 2134
  • [10] C1 polymerisation and related C-C bond forming 'carbene insertion' reactions
    Jellema, Erica
    Jongerius, Anna L.
    Reek, Joost N. H.
    de Bruin, Bas
    CHEMICAL SOCIETY REVIEWS, 2010, 39 (05) : 1706 - 1723
12345