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

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‐com...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2022-12, Vol.11 (12), p.n/a
Main 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
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromides
Carbonylation
Carbonyls
Chemical reactions
Cross coupling
Cross-electrophile Coupling
Halides
Iodides
Ketones
Magnesium
Nucleophiles
Organic chemistry
Palladium
Reagents
Reducing agents
Zinc
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Summary: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. 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 alkyl or aryl alkenyl ketones has been developed. This three‐component carbonylative reaction enables the construction of valuable aryl alkyl/alkenyl ketone derivatives (60 examples, 56–95% yields) with excellent chemoselectivity and functional group tolerance.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200243