The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4 ) 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-SO2 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-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (n class="Chemical">Pyry-BF4 ) 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-SO2 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-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
Authors: Jennie Liao; Corey H Basch; Megan E Hoerrner; Michael R Talley; Brian P Boscoe; Joseph W Tucker; Michelle R Garnsey; Mary P Watson Journal: Org Lett Date: 2019-03-27 Impact factor: 6.005
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Authors: Nicola L Bell; Chao Xu; James W B Fyfe; Julien C Vantourout; Jeremy Brals; Sonia Chabbra; Bela E Bode; David B Cordes; Alexandra M Z Slawin; Thomas M McGuire; Allan J B Watson Journal: Angew Chem Int Ed Engl Date: 2021-02-26 Impact factor: 15.336