Synthesis of benzene- and pyridinediboronic acids via organotin compounds

被引:23
作者
Mandolesi, SD
Vaillard, SE
Podestá, JC
Rossi, RA
机构
[1] Univ Nacl Sur, Dept Quim, RA-8000 Bahia Blanca, Argentina
[2] Univ Nacl Sur, CONICET, RA-8000 Bahia Blanca, Argentina
[3] Univ Nacl Cordoba, Fac Ciencias Quim, Dept Quim Organ, INFIQC UNC CONICET, RA-5000 Cordoba, Argentina
关键词
D O I
10.1021/om020163r
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1,4- and 1,3-Bis(trimethylstannyl)benzenes as well as 2,5- and 2,6-bis(trimethylstannyl)pyridines react with borane in THF to give intermediates which on hydrolysis lead to benzene- and pyridinediboronic acids in 79-83% yield. While oxidation of the benzenediboronic acids with alkaline hydrogen peroxide gives the corresponding 1,3- and 1,4-dihydroxybenzenes, the pyridinediboronic acids lead via a double Suzuki reaction with 4-iodoanisole to 2,5- and 2,6-bis(4-methoxyphenyl)-pyridines and react with pinacol to give the corresponding pyridine-2,5-pinacol and pyridine-2,6-pinacol diboronic esters.
引用
收藏
页码:4886 / 4888
页数:3
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