Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes To Generate Dialkyl Ketones
- 21 November 2019
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 21 (24) , 9940-9944
Abstract
A general protocol for the hydroacylation of styrenes from aliphatic carboxylic acids is reported. These reactions proceed via β-scission of a phosphoranyl radical that is accessed by photoredox catalysis, followed by addition of the resulting acyl radical to the styrenyl olefin. We show that phosphine tunability is critical for efficient intermolecular coupling due to competitive quenching of the photocatalyst by the olefin. Primary, secondary, and structurally rigid tertiary carboxylic acids all generate valuable unsymmetrical dialkyl ketones.Keywords
Funding Information
- National Institute of General Medical Sciences (R35 GM126986)
This publication has 39 references indexed in Scilit:
- Recent methods for the synthesis of α-acyloxy ketonesOrganic & Biomolecular Chemistry, 2018
- Mechanistic insights into hydroacylation with non-chelating aldehydesChemical Science, 2014
- 4.17 Hydroacylation of Alkenes, Alkynes, and Allenes2014
- Catalytic intermolecular hydroacylation of C–C π-bonds in the absence of chelation assistanceChemical Science, 2012
- Transition Metal Catalyzed Alkene and Alkyne HydroacylationChemical Reviews, 2009
- Metal−Organic Cooperative Catalysis in C−H and C−C Bond Activation and Its Concurrent RecoveryAccounts of Chemical Research, 2008
- Assembly-Line Enzymology for Polyketide and Nonribosomal Peptide Antibiotics: Logic, Machinery, and MechanismsChemical Reviews, 2006
- Ruthenium complex catalyzed intermolecular hydroacylation and transhydroformylation of olefins with aldehydesThe Journal of Organic Chemistry, 1990
- Dodecacarbonyltriruthenium catalyzed one-to-one addition of N-substituted formamide to olefinsJournal of Organometallic Chemistry, 1987
- The chemistry of acyl radicalsReviews on Reactive Species in Chemical Reactions, 1973