Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

被引:318
作者
Murphy, Jaclyn M.
Liao, Xuebin
Hartwig, John F.
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[2] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/ja076498n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the meta halogenation of 1,3-disubstituted arenes to form 3,5-disubstituted aryl bromides and chlorides by using iridium-catalyzed arene borylation chemistry. Iridium-catalyzed borylation of arenes with B(2)pin(2), followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding aryl halides. A variety of arenes containing alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols were converted to the corresponding 3,5-disubstituted aryl bromides and chlorides in yields ranging from 46% to 85%. In addition, 2,6-disubstituted and 3-substituted pyridines were converted to the 4-halo and 5-halopyridines, respectively. The utility of this methodology was demonstrated by the formal conversion of nicotine to Altinicline in three steps with an overall yield of 61% using meta bromination of nicotine as the first step.
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页码:15434 / +
页数:3
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