Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using α-(phenylthio)isobutyrophenone

被引：43
作者：
Arisawa, Mieko [1 ]
Toriyama, Fumihiko [2 ]
Yamaguchi, Masahiko [1 ,3 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Daiichi Sankyo Co Ltd, Proc Technol Res Labs, Hiratsuka, Kanagawa 2540014, Japan
[3] Tohoku Univ, Aoba Ku, WPI Adv Inst Mat Res, Sendai, Miyagi 9808577, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 18期
关键词：
Phenylthiolation; Rhodium catalyst; Heteroaromatics; C-H activation; Equilibrium; Benzothiazole; C-H BONDS; ORGANOSULFUR COMPOUNDS; EQUILIBRIUM ACIDITIES; ARYL IODIDES; EFFICIENT; THIOLS; DISULFIDES; THIOETHERS; INDOLES; SULFENYLATION;
D O I：
10.1016/j.tetlet.2011.02.077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of catalytic amounts of RhH(PPh3)(4) and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with alpha-(phenylthio)isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds. (C) 2011 Published by Elsevier Ltd.
引用
收藏
页码：2344 / 2347
页数：4
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