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Direct B ‐Alkyl Suzuki–Miyaura Cross‐Coupling of Trialkyl‐ boranes with Aryl Bromides in the Presence of Unmasked Acidic or Basic Functions and Base‐Labile Protections under Mild Non‐Aqueous Conditions
Author(s) -
Wang Bing,
Sun HuiXia,
Sun ZhiHua,
Lin GuoQiang
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800630
Subject(s) - chemistry , aryl , boranes , alkyl , anhydrous , aqueous solution , base (topology) , bromide , organic chemistry , combinatorial chemistry , medicinal chemistry , boron , mathematical analysis , mathematics
An efficient and chemoselective palladium‐catalyzed direct B ‐alkyl Suzuki–Miyaura cross‐coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non‐aqueous conditions are compatible with aldehydes, ketones, nitriles, chloro substitution as well as base‐labile phenolic Piv and TBS protecting groups. The anhydrous conditions were found to be advantageous for aryl bromide substrates. A potent CEPT inhibitor was efficiently synthesised using this protocol.