From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy.

Authors :: Xi X
Luo Y
Li W
Xu M
Zhao H
Chen Y
Zheng S
Qi X
Yuan W
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Jan 17; Vol. 61 (3), pp. e202114731. Date of Electronic Publication: 2021 Dec 02.
Publication Year :: 2022
Abstract: A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni <superscript>0</superscript> /Ni <superscript>I</superscript> /Ni <superscript>III</superscript> pathway for ketone formation.<br /> (© 2021 Wiley-VCH GmbH.)

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