Formal Carbene C-H Bond Insertion in the Cu(I)-Catalyzed Reaction of Bis(trimethylsilyl)diazomethane with Benzoxazoles and Oxazoles

被引：22
|
作者：
Wang, Shuai [1 ,2 ]
Xu, Shuai [1 ,2 ]
Yang, Cheng [1 ,2 ]
Sun, Hanli [1 ,2 ]
Wang, Jianbo [1 ,2 ,3 ]
机构：
[1] Peking Univ, Coll Chem, BNLMS, Minist Educ, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
关键词：
PETERSON OLEFINATIONS; N-TOSYLHYDRAZONES; METAL CARBENE; REAGENTS; DERIVATIVES; SI;
D O I：
10.1021/acs.orglett.9b00391
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu(I)-catalyzed cross-coupling reaction of bis(trimethylsilyl)diazomethane and benzoxazoles/oxazoles is reported. A wide range of functional groups can be tolerated in this transformation. This reaction provides a new method to directly introduce a 1,1-bis(trimethylsilyl)methyl group into heteroaromatic C-H bonds. Subsequent transformations of 1,1-bis(trimethylsilyl)-methylated heteroaromatic compounds are also presented.
引用
收藏
页码：1809 / 1812
页数：4
相关论文
共 50 条
  • [1] Formal Carbene Insertion into C-C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters
    Xia, Ying
    Liu, Zhenxing
    Liu, Zhen
    Ge, Rui
    Ye, Fei
    Hossain, Mohammad
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (08) : 3013 - 3015
  • [2] Theoretical studies on the C-H bond insertion reaction of carbenes with ethers(I) - Insertion reaction of carbene with dimethyl ether
    Lin, QJ
    Feng, DC
    Wang, HJ
    Cai, ZT
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1999, 20 (11): : 1750 - 1753
  • [3] Cu/PCy3-Catalyzed Formal Carbene Insertion into Electron-Deficient C-H Bonds
    Ren, Yuan-Yuan
    Mao, Hong-Xiang
    Hu, Meng-Yang
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    CHEMCATCHEM, 2020, 12 (17) : 4267 - 4271
  • [4] C-H Bond Functionalization of Benzoxazoles with Chromium(0) Fischer Carbene Complexes
    Hu, Fangdong
    Yang, Jinghui
    Xia, Ying
    Ma, Chen
    Xia, Haiping
    Zhang, Yan
    Wang, Jianbo
    ORGANOMETALLICS, 2016, 35 (10) : 1409 - 1414
  • [5] FORMAL INSERTION OF ACETYLIDE INTO A C-H BOND TO GIVE A BIS(DIPHENYLPHOSPHINO)PROPENYL LIGAND
    JENNINGS, MC
    MANOJLOVICMUIR, L
    PUDDEPHATT, RJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) : 745 - 746
  • [6] Copper-Catalyzed Direct C-H Bond Arylation of Benzoxazoles with Anilines
    Feng, Pengju
    Ma, Guojian
    Zhang, Tianyu
    Wang, Changwei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (04) : 788 - 792
  • [7] Ir(III)-Catalyzed Aromatic C-H Bond Functionalization via Metal Carbene Migratory Insertion
    Xia, Ying
    Liu, Zhen
    Feng, Sheng
    Zhang, Yan
    Wang, Jianbo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01): : 223 - 236
  • [8] C-H bond functionalization based on metal carbene migratory insertion
    Hu, Fangdong
    Xia, Ying
    Ma, Chen
    Zhang, Yan
    Wang, Jianbo
    CHEMICAL COMMUNICATIONS, 2015, 51 (38) : 7986 - 7995
  • [9] Chemoselective Intramolecular Formal Insertion Reaction of Rh-Nitrenes into an Amide Bond Over C-H Insertion
    Kono, Masato
    Harada, Shingo
    Nemoto, Tetsuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (12) : 3119 - 3124
  • [10] IRON CATALYZED INSERTION OF SULFUR INTO THE NONACTIVATED C-H BOND
    BALAVOINE, G
    BARTON, DHR
    GREF, A
    LELLOUCHE, I
    TETRAHEDRON, 1992, 48 (10) : 1883 - 1894
12345