Abstract
Transition metal-catalyzed cross-electrophile coupling of two electrophiles has proved to be a powerful and step-economic strategy for the construction of C–C bonds in organic synthesis. Despite the considerable advances, cross-electrophile coupling of sp2-hybridized carboxylic acid derivatives via a decarbonylative fashion remains a formidable challenge. Herein, we disclose a chemoselective C(sp2)–C(sp2) doubly decarbonylative cross-electrophile coupling of aroyl fluorides with a wide range of aryl and alkenyl thioesters by palladium catalysis. The catalytic protocol provides an alternative route for the efficient synthesis of biaryls and stilbene derivatives owing to wide accessibility, natural abundance and stability of carboxylic acid and relevant derivatives. The combination of a series of experiments and theoretical calculations reveals that conversion of aroyl fluorides into the corresponding thioesters, chloride anion in catalyst PdCl2 and in situ generated Zn(II) reagents play the crucial roles in the current cross-coupling reactions.
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