Coupling of heteroaryl chlorides with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium(II) dichloride

✍ Scribed by M.B. Mitchell; P.J. Wallbank

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 227 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79700-0

✦ Synopsis

The cross-coupling of arylhnronic acids with a variety of x-deficient hcteroaryl chlorides has been shown to occur in high yield in the presence of [I ,4-his-(diphenylphnsphine)butanelpalladium(II) dichloride as catalyst.

AS part of a programme of work to identify efficient, cost-effective synthetic routes to myl-substituted hcteroaryl compounds ol' medicinal interest, we considered the synthesis of these compounds by a palladium mediated cross-coupling approach. A variety of organometallic species have b~cn crnploycd successftllly for the synthesis of biaryl compoundsk using this strategy. We selected boron as the organometallic of choice since arylboronic acids are isolable, stable compounds which can be readily prcparcd, 'L and furthermore it was hoped that rheir nonbasil: nature would offer the possibility of carrying out reactions on substrates b+zuing labile protons. At the start of our work, a review of the literature revealed that with one exception,3 rhe reported examples of palladium catalyxed cross-coupling with arylboronic: acids all used aryl or hctcroaryl bromides or iodides.2b. 2C. 4