cs7b00928_si_002.cif (601.75 kB)
Selective Piperidine Synthesis Exploiting Iodine-Catalyzed Csp3–H Amination under Visible Light
dataset
posted on 2017-05-10, 00:00 authored by Hongwei Zhang, Kilian MuñizA 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.