Functionalization of Carbonyl Compounds via Photoredox Organocatalysis

Abstract

In recent years, a methodology merging photoredox catalysis with organocatalysis termed “photoredox organocatalysis” has emerged to allow the direct, selective and efficient functionalization of the α/β‐C of carbonyl compounds under mild reaction condition. In this review, photophysics background of photoredox catalysis is introduced, followed by a report on recent advances in direct α‐ and β‐functionalization of carbonyls with photoredox organocatalysis methodology. With this different reaction modes, valuable synthetic targets including different α/β‐functionalized carbonyls are accessible.

Photocatalytic Biheterocyclization of 1,7-Diynes for Accessing Skeletally Diverse Tricyclic 2-Pyranones

“…Consequently, a great number of seminal reports have demonstrated the significant applicability of VLPC reactions in synthetic chemistry, making it more versatile and workable . Most existing photocatalytic transformations can be classified into the following reaction categories: [2 + 2] cycloadditions, α-functionalization of carbonyls or amines, dehalogenation reactions, radical C–H functionalizations of arenes, and redox-neutral annulations . Among them, the latter offers useful and flexible access to build up functional cyclic molecules that are difficult to fabricate from thermal processes.…”

Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides

“…Visible-light-driven photoredox catalysis has been well-established as a powerful tool in the construction of carbon–carbon and carbon–heteroatom bonds in organic synthesis over the past decade . The merging of photoredox catalysis with transition metal catalysis has shed new light on transition metal catalysis, by not only providing new coupling partners but also altering the catalytic cycles .…”

Asymmetric cross Rauhut–Currier reactions of vinyl ketones with carbonylpara-quinone methidesviaphosphine catalysis

“…The asymmetric catalytic α-functionalization of carbonyl compounds is an important cornerstone and attractive goal in organic chemistry. 1 Therefore, many protocols have been developed in this field (Scheme 1), such as transition-metal-catalyzed carbonyl α-C(sp 3 )–H coupling, 2 chiral-amine-catalyst-mediated enolate or enamine addition, 3 the photoredox coupling of carbonyl compounds with various partners, and so on, 4,5 to fulfill the increased demand for the synthesis of complex natural products and bioactive pharmaceuticals. It is predicted that obtaining more novel carbonyl synthons will allow more fascinating molecular architectures to be produced.…”