Three-component coupling using arynes and aminosilanes for ortho-selective double functionalization of aromatic skeletons

被引:43
作者
Morishita, Takami [1 ]
Fukushima, Hiroyuki [1 ]
Yoshida, Hiroto [1 ]
Ohshita, Joji [1 ]
Kunai, Atsutaka [1 ]
机构
[1] Hiroshima Univ, Dept Appl Chem, Grad Sch Engn, Higashihiroshima 7398527, Japan
关键词
D O I
10.1021/jo800761b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arynes were found to couple with aminosilanes and carbonyl compounds in the presence of benzoic acid to provide 2-aminobenzhydrols. Sulfonylimines could also be applied to the reaction, enabling amino and aminomethyl moieties to be incorporated into contiguous positions of aromatic skeletons. Only a small amount of the three-component coupling product was obtained in the absence of benzoic acid, which confirms its vital role in the present reaction.
引用
收藏
页码:5452 / 5457
页数:6
相关论文
共 53 条
[51]   Insertion of arynes into carbon-halogen σ-bonds:: regioselective acylation of aromatic rings [J].
Yoshida, Hiroto ;
Mimura, Yasuhiro ;
Ohshita, Joji ;
Kunai, Atsutaka .
CHEMICAL COMMUNICATIONS, 2007, (23) :2405-2407
[52]   Straightforward construction of diarylmethane skeletons via aryne insertion into carbon-carbon σ-bonds [J].
Yoshida, Hiroto ;
Watanabe, Masahiko ;
Morishita, Takami ;
Ohshita, Joji ;
Kunai, Atsutaka .
CHEMICAL COMMUNICATIONS, 2007, (15) :1505-1507
[53]   CO2 incorporation reaction using arynes:: Straightforward access to benzoxazinone [J].
Yoshida, Hiroto ;
Fukushima, Hiroyuki ;
Ohshita, Joji ;
Kunai, Atsutaka .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11040-11041