Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis
Open Access
- 17 September 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 136 (39), 13606-13609
- https://doi.org/10.1021/ja508317j
Abstract
A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions.Keywords
Funding Information
- Division of Chemistry (CHE-1058855)
This publication has 49 references indexed in Scilit:
- Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp 3 -carbons with aryl halidesScience, 2014
- Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysisScience, 2014
- Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring ExpansionJournal of the American Chemical Society, 2014
- Combining Gold and Photoredox Catalysis: Visible Light-Mediated Oxy- and Aminoarylation of AlkenesJournal of the American Chemical Society, 2013
- Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3IJournal of the American Chemical Society, 2012
- Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathwaysChemical Science, 2012
- Dual Catalysis: Combination of Photocatalytic Aerobic Oxidation and Metal Catalyzed Alkynylation Reactions—C-C Bond Formation Using Visible LightChemistry – A European Journal, 2012
- Room-Temperature C–H Arylation: Merger of Pd-Catalyzed C–H Functionalization and Visible-Light PhotocatalysisJournal of the American Chemical Society, 2011
- Decarboxylative coupling reactions: a modern strategy for C–C-bond formationChemical Society Reviews, 2011
- Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation ReactionsChemical Reviews, 2011