Palladium-catalyzed C-H functionalization of acyldiazomethane and tandem cross-coupling reactions

Journal of the American Chemical Society
Fei YeJianbo Wang

Abstract

Palladium-catalyzed C-H functionalization of acyldiazomethanes with aryl iodides has been developed. This reaction is featured by the retention of the diazo functionality in the transformation, thus constituting a novel method for the introduction of diazo functionality to organic molecules. Consistent with the experimental results, the density functional theory (DFT) calculation indicates that the formation of Pd-carbene species in the catalytic cycle through dinitrogen extrusion from the palladium ethyl diazoacetate (Pd-EDA) complex is less favorable. The reaction instead proceeds through Ag2CO3 assisted deprotonation and subsequently reductive elimination to afford the products with diazo functionality remained. This C-H functionalization transformation can be further combined with the recently evolved palladium-catalyzed cross-coupling reaction of diazo compounds with aryl iodides to develop a tandem coupling process for the synthesis of α,α-diaryl esters. DFT calculation supports the involvement of Pd-carbene as reactive intermediate in the catalytic cycle, which goes through facile carbene migratory insertion with a low energy barrier (3.8 kcal/mol).

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Citations

Dec 17, 2015·The Journal of Organic Chemistry·Santosh D Jadhav, Anand Singh
Sep 24, 2015·Journal of the American Chemical Society·Guiping QinHanmin Huang
Feb 22, 2017·Chemical Communications : Chem Comm·Marta Pérez-GómezJosé-Antonio García-López
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Jul 8, 2017·Organic & Biomolecular Chemistry·Yujie LiangSiwei Bi
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Apr 6, 2021·Organic Letters·Joomyung V Jun, Ronald T Raines
Jun 24, 2021·Journal of the American Chemical Society·Yifan PingJianbo Wang
Jul 8, 2021·Accounts of Chemical Research·Xiaotian Qi, Yu Lan
Dec 21, 2018·Organic Letters·Christopher JanotChristophe Aïssa
Dec 7, 2019·The Journal of Organic Chemistry·Christopher JanotChristophe Aïssa

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