A. Bouillon, J. Lancelot, V. Collot
Apr 1, 2002
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Journal
Tetrahedron
Abstract
Abstract This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4 , 7 , 10 , 13 , 15 . These compounds are prepared taking into account a regioselective halogen–metal exchange using n BuLi or a regioselective ortho -lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.