Premium
Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
Author(s) -
Moser Daniel,
Duan Yaya,
Wang Feng,
Ma Yuanhong,
O'Neill Matthew J.,
Cornella Josep
Publication year - 2018
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.201806271
Subject(s) - reagent , tetrafluoroborate , surface modification , chemistry , derivatization , functional group , salt (chemistry) , nucleophile , combinatorial chemistry , molecule , nucleophilic substitution , medicinal chemistry , organic chemistry , ionic liquid , catalysis , high performance liquid chromatography , polymer
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry‐BF 4 ) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C−N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C−O, C−N, C−S, or C−SO 2 R bonds are disclosed herein. In contrast to C−N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional‐group tolerance. In addition to small‐molecule derivatization, Pyry‐BF 4 allows the introduction of functional groups in a late‐stage fashion to furnish highly functionalized structures.