Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds

被引：43
作者：
Chen, Xun [1 ]
Xie, Ying [1 ]
Xiao, Xinsheng [1 ]
Li, Guoqiang [2 ]
Deng, Yuanfu [1 ]
Jiang, Huanfeng [1 ]
Zeng, Wei [1 ]
机构：
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510641, Guangdong, Peoples R China
[2] Jinan Univ, Anal & Testing Ctr, Guangzhou 510632, Guangdong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 83期
关键词：
C-H FUNCTIONALIZATION; INSERTION REACTIONS; ONE-POT; CYCLIZATION; ALKYNES; CYCLOPROPANATION; DIAZOOXINDOLES; KETOIMINES; ALDEHYDES; ACCESS;
D O I：
10.1039/c5cc06428g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Rh(III)-catalyzed cross-coupling/cyclization cascade of alpha-imino Csp(3)-H bonds with donor/acceptor alpha-acyl diazocarbonyl compounds has been developed. This novel transformation involves ligand-directed Csp(3)-H bond functionalization with carbenoids under the pyridine-chelation assistance, and offered an efficient access to synthetically versatile polysubstituted N-(2-pyridyl)pyrroles with a broad range of functional group tolerance.
引用
收藏
页码：15328 / 15331
页数：4
相关论文
共 52 条
  • [21] A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C-H Activation
    Hyster, Todd K.
    Ruhl, Kyle E.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5364 - 5367
  • [22] Development of a Povarov Reaction/Carbene Generation Sequence for Alkenyldiazocarbonyl Compounds
    Jadhav, Appaso Mahadev
    Pagar, Vinayak Vishnu
    Liu, Rai-Shung
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (47) : 11809 - 11813
  • [23] One-Pot, Two-Step Conversion of Aldehydes to Phosphonyl- and Sulfonylpyrazoles Using Bestmann-Ohira Reagent
    Kumar, Rahul
    Verma, Deepti
    Mobin, Shaikh M.
    Namboothiri, Irishi N. N.
    [J]. ORGANIC LETTERS, 2012, 14 (16) : 4070 - 4073
  • [24] Catalytic Enantioselective Carbon Insertion into the β-Vinyl C-H Bond of Cyclic Enones
    Lee, Sung Il
    Hwang, Geum-Sook
    Ryu, Do Hyun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) : 7126 - 7129
  • [25] Cu(I)-Catalyzed Transannulation of N-Heteroaryl Aldehydes or Ketones with Alkylamines via C(sp3)-H Amination
    Li, Mingyang
    Xie, Ying
    Ye, Yong
    Zou, Yong
    Jiang, Huanfeng
    Zeng, Wei
    [J]. ORGANIC LETTERS, 2014, 16 (23) : 6232 - 6235
  • [26] Stereoselective Rh2(S-IBAZ)4-Catalyzed Cyclopropanation of Alkenes, Alkynes, and Allenes: Asymmetric Synthesis of Diacceptor Cyclopropylphosphonates and Alkylidenecyclopropanes
    Lindsay, Vincent N. G.
    Fiset, Dominic
    Gritsch, Philipp J.
    Azzi, Soula
    Charette, Andre B.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1463 - 1470
  • [27] Pd-Catalyzed Tandem Cyclization of Ethyl Glyoxalate and Amines: Rapid Assembly of Highly Substituted Cyclic Dehydro-α-Amino Acid Derivatives
    Luo, Yueting
    Lu, Xiaoxia
    Ye, Yong
    Guo, Ya
    Jiang, Huanfeng
    Zeng, Wei
    [J]. ORGANIC LETTERS, 2012, 14 (22) : 5640 - 5643
  • [28] Reaction Design, Discovery, and Development as a Foundation to Function-Oriented Synthesis
    Micalizio, Glenn C.
    Hale, Sarah B.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) : 663 - 673
  • [29] First example of regiospecific intermolecular C-H insertion reactions of cyclic rhodium carbenoids:: novel synthesis of 3-indol-3′-yloxindoles
    Muthusamy, S
    Gunanathan, C
    Babu, SA
    Suresh, E
    Dastidar, P
    [J]. CHEMICAL COMMUNICATIONS, 2002, (08) : 824 - 825
  • [30] Muthusamy S., 2004, SYNLETT, P639
123456