Abstract
Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.
Highlights
Carbonyl-containing compounds, such as ketones, esters and amides, widely exist in numerous biologically important natural products, functional materials as well as pharmaceuticals [1,2,3,4,5].The development of efficient methods toward synthesis of these substantial compounds has been intensively pursued by synthetic chemists over the past decades
Radical carbonylation promoted by transition metals (Pd, Mn, Co, Ni, Ru, Rh etc.), external oxidants or thermal initiation has been well-established for the preparation of carbonyl compounds with high efficiency [6,7,8,9,10,11,12]
We mainly summarize recent advances in the field of visible light-induced radical carbonylative synthesis of oxygen and nitrogen heterocycles with an emphasis on the catalytic system, scope and reaction mechanism
Summary
Carbonyl-containing compounds, such as ketones, esters and amides, widely exist in numerous biologically important natural products, functional materials as well as pharmaceuticals [1,2,3,4,5]. The pioneering examples are typically mercury and polyoxotungstate-photosensitized alkane carbonylation, metal-carbonyl catalyzed radical carbonylation and radical/Pd-combined carbonylation Despite these impressive advances, the requirement of high-energy UV irradiation, poor selectivity or low efficiency profoundly limits their broad applications in practical synthesis. Various radical species can be formed in a mild and controllable fashion, which enables the precise synthesis of high value-added products In this context, acyl radicals are commonly generated by the addition of alkyl or aryl radicals to carbon monoxide (CO) or from single electron transfer (SET) conversion of aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids (Scheme 1) [31]. 2 of principal achievements are partitioned into the sections organized based on different acyl radical carbonylation and atom transfer radical carbonylation have been comprehensively reviewed radical before precursors.
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