Palladium(II)-Catalyzed Decarboxylative Difunctionalization of Alkynoic Acids To Access (E)-β-Sulfonylacrylamides and DFT Study

被引：3

作者：

Tripathi, Shashank ^{[1
,2
]}

Kumar, Monty ^{[1
,2
]}

Shivhare, Ayush ^{[3
]}

Kant, Ruchir ^{[4
]}

Deshmukh, Milind M. ^{[3
]}

Srivastava, Ajay Kumar ^{[1
,2
]}

机构：

[1] CSIR, Cent Drug Res Inst, Med & Proc Chem, Lucknow 226031, India

[2] AcSIR, Ghaziabad 201002, India

[3] Dr Harisingh Gour Vishwavidyalaya Cent Univ, Dept Chem, Sagar 470003, India

[4] CSIR, Biochem & Struct Biol, Cent Drug Res Inst, Lucknow 226031, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 36期

关键词：

VINYL SULFONES; BETA-LACTAMS; CONSTRUCTION; EFFICIENT;

D O I：

10.1021/acs.orglett.3c02415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium(II)-catalyzed regio- and stereoselective difunctionalization of alkynoic acids has been achieved using sodium sulfinates and isocyanides to synthesize (E)-ss-sulfonylacrylamides. The reaction proceeds via decarboxylative isocyanide addition, followed by sulfonylation. This three-component process works well with aromatic, heteroaromatic, and aliphatic alkynoic acids with good functional group tolerance and excellent regio- and stereoselectivity. DFT calculations were carried out to explain the reaction mechanism and the stereoselective formation of (E)-ss-sulfonylacrylamides.

引用

页码：6638 / 6642

页数：5

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