%0 Journal Article
%A Zhang, Hongwei
%A Muñiz, Kilian
%D 2017
%T Selective Piperidine Synthesis Exploiting Iodine-Catalyzed
Csp3–H Amination under Visible Light
%U https://acs.figshare.com/articles/journal_contribution/Selective_Piperidine_Synthesis_Exploiting_Iodine-Catalyzed_C_sub_sp_sub_sup_3_sup_H_Amination_under_Visible_Light/5011982
%R 10.1021/acscatal.7b00928.s001
%2 https://acs.figshare.com/ndownloader/files/8447093
%K light initiation
%K free-radical-promoted piperidine formation
%K iodine catalyst
%K terminal oxidant
%K halogen coordination
%K 30 applications
%K pyrrolidine synthesis
%K sp
%K Visible Light
%K nitrogen intermediates
%K piperidine formation
%K hydrocarbon amination reaction
%X A route
to selective piperidine formation through intramolecular
catalytic Csp3–H amination is described.
This hydrocarbon amination reaction employs a homogeneous iodine catalyst
derived from halogen coordination between molecular iodine and a terminal
oxidant. It relies on visible light initiation and proceeds within
two catalytic cycles that comprise a radical C–H functionalization
and an iodine-catalyzed C–N bond formation. Under these conditions,
the commonly observed preference for pyrrolidine synthesis based on
halogenated nitrogen intermediates within the Hofmann–Löffler
domain is effectively altered in favor of a free-radical-promoted
piperidine formation. The protocol is demonstrated for a total of
30 applications.
%I ACS Publications