Silver-Mediated Oxidative C-H/P-H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides

被引:269
作者
Chen, Yun-Rong [1 ]
Duan, Wei-Liang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
INTRAMOLECULAR RADICAL TRANSFER; N BOND FORMATION; O BOND; INDOLES; CYCLIZATION; ALKYNES; PHOSPHONATION; ANNULATIONS; PHOSPHORUS; ENAMINES;
D O I
10.1021/ja407373g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Ag-mediated C-H/P-H functionalization reaction of arylphosphine oxides with internal alkynes was described for the direct preparation of benzo[b]phosphole oxides with a high yield. An unusual aryl migration on the P-atom derived from a C-P bond cleavage and a new C-P bond formation was also observed and demonstrated to proceed via the radical process.
引用
收藏
页码:16754 / 16757
页数:4
相关论文
共 71 条
[1]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[2]   Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends [J].
Albrecht, Martin .
CHEMICAL REVIEWS, 2010, 110 (02) :576-623
[3]  
Bansal RK, 2010, TOP HETEROCYCL CHEM, V21, P1, DOI 10.1007/978-3-642-12254-5
[4]   Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].
Bernini, Roberta ;
Fabrizi, Giancarlo ;
Sferrazza, Alessio ;
Cacchi, Sandro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081
[5]  
Borner A., 2008, Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications
[6]   Synthesis using aromatic homolytic substitution - recent advances [J].
Bowman, W. Russell ;
Storey, John M. D. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) :1803-1822
[7]   Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes [J].
Chen, Jinlei ;
Song, Guoyong ;
Pan, Cheng-Ling ;
Li, Xingwei .
ORGANIC LETTERS, 2010, 12 (23) :5426-5429
[8]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[9]   Pd(II)-Catalyzed Enantioselective C-H Activation/C-O Bond Formation: Synthesis of Chiral Benzofuranones [J].
Cheng, Xiu-Fen ;
Li, Yan ;
Su, Yi-Ming ;
Yin, Feng ;
Wang, Jian-Yong ;
Sheng, Jie ;
Vora, Harit U. ;
Wang, Xi-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) :1236-1239
[10]   Synthesis of biaryls by intramolecular radical transfer in phosphinates [J].
Clive, DLJ ;
Kang, SZ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) :6083-6091