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N ‐(Acyloxy)phthalimides as Redox‐Active Esters in Cross‐Coupling Reactions
Author(s) -
Murarka Sandip
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701615
Subject(s) - chemistry , redox , phthalimides , coupling reaction , combinatorial chemistry , photochemistry , computational chemistry , organic chemistry , catalysis , phthalimide
Recent years have witnessed a resurgence of novel, efficient and practical protocols for radical‐mediated cross‐coupling reactions involving N ‐(acyloxy)phthalimides (NHPI esters) as redox‐active esters. After the initial discovery of the redox‐active properties of NHPI esters, exciting examples of SET‐based cross‐coupling reactions under thermal or photolytic conditions leading to diverse C–X (X=C, B, Si, Se, S) bonds have been published. The operational simplicity and broad applicability exhibited in redox‐active NHPI ester‐based cross‐couplings bode well for their widespread adoption. The review presented herein covers all the recent developments in the field of redox‐active ester (RAE)‐based cross‐couplings since the initial discovery. Depending on the conditions employed the reactions have been categorized into photoinduced and non‐photoinduced cross‐couplings with representative examples and insightful mechanistic discussions.