Cobalt(III)-Catalyzed Fast and Solvent-Free C-H Allylation of Indoles Using Mechanochemistry

被引:68
作者
Jiang, Xinpeng [1 ]
Chen, Jinkang [1 ]
Zhu, Weijie [1 ]
Cheng, Kang [1 ]
Liu, Yong [1 ]
Su, Wei-Ke [2 ]
Yu, Chuanming [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND ACTIVATION; ALLYLIC ALCOHOLS; COBALT CATALYSIS; ROOM-TEMPERATURE; BALL MILL; FUNCTIONALIZATION; AMIDATION; ARENES; ALKYNES; ISOQUINOLINES;
D O I
10.1021/acs.joc.7b01695
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mechanochemical conditions have been applied to a highly efficient cobalt(III)-catalyzed C-H bond activation for the first time. In a subsequent step to the olefin insertion and beta-oxygen elimination, N-pyrimidinylindoles were allylated with vinylethylene carbonate's in the absence of organic solvent under high-speed ball-milling condition. As the reaction afforded the desired products in up to 98% yields within a short time, this method constitutes an environmentally friendly and powerful alternative to the common solution-based approaches.
引用
收藏
页码:10665 / 10672
页数:8
相关论文
共 70 条
[1]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[2]   Cp*CoIII Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks [J].
Bera, Sourav Sekhar ;
Debbarma, Suvankar ;
Ghosh, Avick Kumar ;
Chand, Santanu ;
Maji, Modhu Sudan .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01) :420-430
[3]   Mechanochemistry: The mechanical activation of covalent bonds [J].
Beyer, MK ;
Clausen-Schaumann, H .
CHEMICAL REVIEWS, 2005, 105 (08) :2921-2948
[4]   Cp*CoIII-Catalyzed Dehydrative C-H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols [J].
Bunno, Youka ;
Murakami, Nanami ;
Suzuki, Yudai ;
Kanai, Motomu ;
Yoshino, Tatsuhiko ;
Matsunaga, Shigeki .
ORGANIC LETTERS, 2016, 18 (09) :2216-2219
[5]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[6]   Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].
Colby, Denise A. ;
Tsai, Andy S. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825
[7]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[8]   C-H Bond Activation Reactions of Ethers That Generate Iridium Carbenes [J].
Conejero, Salvador ;
Paneque, Margarita ;
Poveda, Manuel L. ;
Santos, Laura L. ;
Carmona, Ernesto .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (04) :572-580
[9]   Cp*Rh(III)-Catalyzed Low Temperature C-H Allylation of N-Aryl-trichloro Acetimidamide [J].
Debbarma, Suvankar ;
Bera, Sourav Sekhar ;
Maji, Modhu Sudan .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) :11716-11725
[10]   PALLADIUM-CATALYZED COUPLING OF VINYL EPOXIDES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
TUETING, DR ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4039-4041