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- Title
Palladium‐Catalyzed Carbonylative Cross‐Coupling of Aryl Iodides and Alkenyl Bromides with Benzyl Halides under Reductive Conditions.
- Authors
Lin, Tingzhi; Qian, Pengcheng; Wang, Yan‐En; Ou, Mingjie; Cui, Ning; Ye, Yu; Hua, Rui; Xiong, Dan; Xue, Fei; Walsh, Patrick J.; Mao, Jianyou
- 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.
- Subjects
BENZYL halides; ARYL halides; BENZYL bromide; ARYL iodides; KETONE derivatives; REDUCING agents; NUCLEOPHILES
- Publication
Asian Journal of Organic Chemistry, 2022, Vol 11, Issue 12, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202200243