Aerobic Acyloxylation of Allylic C−H Bonds Initiated by a Pd 0  Precatalyst with 4,5‐Diazafluoren‐9‐one as an Ancillary Ligand | Zendy

Kozack Caitlin V. | Zendy; Sowin Jennifer A. | Zendy; Jaworski Jonathan N. | Zendy; Iosub Andrei V. | Zendy; Stahl Shan S. | Zendy

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Aerobic Acyloxylation of Allylic C−H Bonds Initiated by a Pd 0 Precatalyst with 4,5‐Diazafluoren‐9‐one as an Ancillary Ligand

Author(s) -

Kozack Caitlin V.,

Sowin Jennifer A.,

Jaworski Jonathan N.,

Iosub Andrei V.,

Stahl Shan S.

Publication year - 2019

Publication title -

chemsuschem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 2.412

H-Index - 157

eISSN - 1864-564X

pISSN - 1864-5631

DOI - 10.1002/cssc.201900727

Subject(s) - allylic rearrangement , ligand (biochemistry) , chemistry , palladium , catalysis , medicinal chemistry , stereochemistry , organic chemistry , receptor , biochemistry

Palladium‐catalyzed allylic C−H oxidation has been widely studied, but most precedents use acetic acid as the coupling partner. In this study, a method compatible with diverse carboxylic acid partners has been developed. Use of a Pd 0 precatalyst under aerobic reaction conditions leads to oxidation of Pd 0 by O 2 in the presence of the desired carboxylic acid to generate a Pd II dicarboxylate that promotes acyloxylation of the allylic C−H bond. Good‐to‐excellent yields are obtained with a roughly 1:1 ratio of the alkene and carboxylic acid reagents. Optimized reaction conditions employ 4,5‐diazafluoren‐9‐one (DAF) as a ligand, in combination with a quinone/iron phthalocyanine cocatalyst system to support aerobic catalytic turnover.

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