Catalytic Domino Three‐Component Synthesis of Functionalized Heterocycles from Carbon Dioxide

Author:

Shi Wangyu12,Qiao Chang1,Benet‐Buchholz Jordi1,Kleij Arjan W.13ORCID

Affiliation:

1. Institute of Chemical Research of Catalonia (ICIQ) the Barcelona Institute of Science and Technology Av. Països Catalans 16 43007 – Tarragona Spain

2. Universitat Rovira i Virgili C/Marcel⋅lí Domingo s/n 43007 Tarragona Spain

3. Catalan Institute of Research and Advanced Studies (ICREA) Pg. Lluís Companys 23 08010 Barcelona Spain

Abstract

AbstractA catalytic domino, three‐component reaction has been developed for the transformation of carbon dioxide into functionalized six‐membered cyclic carbonates. The catalytic process combines an initial carboxylative cyclization of β‐epoxy alcohols followed by an oxa‐Michael reaction affording an unparalleled scope of heterocyclic structures. The wide range of functional groups, including free‐alcohols, empowers the access to a range of products including C11‐oxo‐based bicyclic heterocycles. The versatility of these functionalized carbonates is further complemented by a series of synthetic diversifications. Control experiments are consistent with the first step of this domino process being promoted by a binary Lewis acid/base catalyst, while the second stage only requires catalytic base.

Funder

Institució Catalana de Recerca i Estudis Avançats

Publisher

Wiley

Subject

General Energy,General Materials Science,General Chemical Engineering,Environmental Chemistry

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