Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 12, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200243
Keywords
Carbonylation; Cross-electrophile Coupling; Ketones; Palladium; Zinc
Categories
Funding
- National Natural Science Foundation of China [22071107]
- Natural Science Foundation of Jiangsu Province, China [BK20211588, BK20220328]
- Jiangsu Excellent Postdoctoral Program [287706]
- US National Science Foundation [CHE-1902509]
- China Postdoctoral Science Foundation [2022M711596]
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A direct and convenient method for the synthesis of aryl/alkenyl alkyl ketones has been developed. This method overcomes the limitations of previous methods and avoids the use of organometallic reagents.
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.
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