Issue 35, 2023
From the journal:

Organic & Biomolecular Chemistry

Palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides with aryl formates†

Chen Chen, ORCID logo *a   Liying Liu,a   Jin-Ping Liu,a   Jie Ding,a   Chang Ni,a   Chunjie Ni*b  and  Bolin Zhu ORCID logo *a  

* Corresponding authors

a Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China
E-mail: hxxyzbl@tjnu.edu.cn, hxxycc@tjnu.edu.cn

b School of Pharmacy, Yancheng Teachers University, Yancheng 224007, P. R. China
E-mail: nicj@yctu.edu.cn

Abstract

We report a palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides by utilizing aryl formates as convenient CO surrogates. One C–O and two C–C bonds are constructed to give diversiform esterified oxindoles/γ-lactams bearing an all-carbon quaternary stereocenter under gas-free conditions. This transformation features a wide substrate scope and good functional group tolerance and can be easily applied to late-stage functionalization.

Graphical abstract: Palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides with aryl formates

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Article information

DOI
https://doi.org/10.1039/D3OB01149F
Article type
Paper
Submitted
20 Jul 2023
Accepted
11 Aug 2023
First published
14 Aug 2023

Org. Biomol. Chem., 2023,21, 7129-7135

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Palladium-catalyzed Heck-carbonylation of alkene-tethered carbamoyl chlorides with aryl formates

C. Chen, L. Liu, J. Liu, J. Ding, C. Ni, C. Ni and B. Zhu, Org. Biomol. Chem., 2023, 21, 7129 DOI: 10.1039/D3OB01149F

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