Palladium-Catalyzed Carbonylative Cross-Coupling of Aryl Iodides and Alkenyl Bromides with Benzyl Halides under Reductive Conditions

Tingzhi Lin, Pengcheng Qian, Yan-En Wang, Mingjie Ou, Ning Cui, Yu Ye, Rui Hua, Dan Xiong, Fei Xue, Patrick Joseph Walsh, Jianyou Mao

aTechnical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu

Road, Nanjing 211816, P.R. China

Abstract: A direct and convenient method for the palladium-catalyzed reductive cross-coupling of aryl iodides or alkenyl bromides and secondary benzyl halides under ambient CO pressure to generate a diverse array of aryl/alkenyl alkyl ketones has been developed. This strategy successfully achieves a three-component carbonylative reaction with Zn as the reducing agent for C–C bond formation, overcoming the well-known homocoupling of aryl or alkenyl halides, direct cross-coupling between two different electrophiles and other carbonylative coupling reactions. In addition, this method avoids use of preformed organometallic nucleophiles, such as organo-magnesium, zinc and boron reagents. This approach enables the construction of valuable aryl alkyl/alkenyl ketone derivatives (60 examples, 56–95% yields). Reactivity studies indicate that in situ formed benzylic zinc reagents are intermediates in the catalytic system.

Asian Journal of Organic Chemistry/ DOI: 10.1002/ajoc.202200243  (2022年影响因子3.116)

论文链接： https://doi.org/10.1002/ajoc.202200243