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Harnessing Energy‐Transfer in N‐Centered Radical‐Mediated Synthesis of Pyrrolidines
Author(s) -
Fodran Peter,
Wallentin CarlJohan
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000537
Subject(s) - chemistry , atom transfer radical polymerization , photoredox catalysis , diastereomer , surface modification , combinatorial chemistry , catalysis , photochemistry , atom economy , polymerization , organic chemistry , polymer , photocatalysis
Atom transfer radical addition (ATRA), cyclization (ATRC), and polymerization (ATRP) are valuable synthetic methods for the functionalization of olefins. With the advent of photoredox catalysis, visible‐light became a popular tool for the initiation of these reactions. We have developed a protocol that enables easy access to distally functionalized pyrrolidines employing blue‐light mediated atom transfer radical [3+2] cyclization. The reaction is scalable, proceeds at very mild conditions. tolerates various functional groups, and provides the corresponding products in good to excellent yields. If rigid olefins are utilized as the reaction partners, the products can be isolated as single diastereomers. The mechanistic investigations provide strong support for an energy‐transfer mechanism.