Journal
CCS CHEMISTRY
Volume 4, Issue 7, Pages 2469-2480Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202101197
Keywords
metallaphotoredox; decarboxylative acylation; ketones synthesis; dual-catalysis; carboxylic acid
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Funding
- National Natural Science Foundation of China [22001117, 21971108, 21971111, 21732003]
- Natural Science Foundation of Jiangsu Province [BK20190006]
- Fundamental Research Funds for the Central Universities [0205/14380252]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province
- Foundation of Advanced Catalytic Engineering Research Center of the Ministry of Education of Hunan University
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This study reports a novel ketone synthesis method using a photoredox-nickel catalyst to react common aliphatic acids with aromatic and aliphatic thioesters. It efficiently constructs structurally diverse ketones with high yields. The method demonstrates excellent selectivity and functional group compatibility, representing a significant advancement in ketone synthesis.
Ketones serve as one of the most critical building blocks in organic synthesis, involving numerous functional group transformations. Herein, we rep ort an unprecedented photoredox-nickel metallap hotoredox-catalyzed decarboxylative acylation of common aliphatic acids with readily available aromatic and aliphatic thioesters. A wide range of structurally diverse asymmetrical aryl alkyl and dialkyl ketones have been constructed in yields of up to 98% with this strategy. The protocol has excellent reaction selectivity and functional group compatibility, representing a significant step forward in ketone synthesis. The one-pot decarboxylative acylation at the gram scale from two different carbox- synthesis of complex ketones shows its synthetic robustness. Both mechanistic experiments and density functional theory (DFT) calculations suggest that the decarboxylative acylation reaction operates via an underdeveloped Ni( I)-Ni(II)-Ni( I)Ni(III)-Ni(I) catalytic cycle. [GRAPHICS] .
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