10.1021/acscatal.7b00928.s002
Hongwei Zhang
Hongwei
Zhang
Kilian Muñiz
Kilian
Muñiz
Selective Piperidine Synthesis Exploiting Iodine-Catalyzed
C<sub>sp</sub><sup>3</sup>–H Amination under Visible Light
American Chemical Society
2017
light initiation
free-radical-promoted piperidine formation
iodine catalyst
terminal oxidant
halogen coordination
30 applications
pyrrolidine synthesis
sp
Visible Light
nitrogen intermediates
piperidine formation
hydrocarbon amination reaction
2017-05-10 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Selective_Piperidine_Synthesis_Exploiting_Iodine-Catalyzed_C_sub_sp_sub_sup_3_sup_H_Amination_under_Visible_Light/5011979
A route
to selective piperidine formation through intramolecular
catalytic C<sub>sp</sub><sup>3</sup>–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.