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Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation
Author(s) -
Wu Fan,
Alom NurE,
Ariyarathna Jeewani P.,
Naß Johannes,
Li Wei
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904662
Subject(s) - olefin fiber , regioselectivity , cycloaddition , chemistry , intermolecular force , urea , functional group , selectivity , combinatorial chemistry , catalysis , organic chemistry , molecule , polymer
A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio‐ and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional‐group tolerance.