Rhodium(II)-Catalyzed Reaction of 1-Tosyl-1,2,3-triazoles with Morita-Baylis-Hillman Adducts: Synthesis of 3,4-Fused Pyrroles

Chemistry, an Asian Journal
Renmeng JiaWei-Ping Deng

Abstract

A cascade reaction of rhodium azavinylcarbenes with Morita-Baylis-Hillman (MBH) adducts enables a novel synthetic approach to 3,4-fused pyrroles. The cascade reaction begins with the insertion of O-H bond into rhodium azavinylcarbenes, subsquent sigmatropic rearrangement provides substituted α,β-unsaturated cyclic ketone intermediates. Then the intramolecular aza Michael addition/oxidative aromatization sequence give rise to a wide range of 3,4-fused pyrroles in good yields, and with excellent functional group compatibility.

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Citations

May 20, 2020·Chemistry : a European Journal·Wenbo Li, Junliang Zhang
Jun 25, 2021·Chemical Science·Alejandro Guarnieri-IbáñezJérôme Lacour
Sep 4, 2021·Chemistry, an Asian Journal·Hyeongsu KimJu Hyun Kim
Nov 19, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Kuntal Pal, Chandra M R Volla

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