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- W2889608267 abstract "The Pd-catalyzed carbonylation of cyclic β-chloro enones using simple phosphine ligands is described. Screening identified P(Me)(t-Bu)2 as the most general ligand for an array of chloro enone electrophiles. The reaction scope has been evaluated on a milligram scale across 80 examples, with excellent reactivity observed in nearly every case. Carbonylation can be achieved even in the presence of potentially sensitive or inhibitory functional groups, including basic nitrogens as well as aryl chlorides or bromides. Twenty examples have been run on a gram scale, demonstrating scalability and practical utility. Using P(Me)(t-Bu)2, the reaction rate depends on both nucleophile and electrophile identity, with completion times varying between 3 and >18 h under a standard set of conditions. Switching to P(t-Bu)3 for the carbonylation of 3-chlorocyclohex-2-enone with methanol results in a dramatic rate increase, enabling effective catalysis with kinetics consistent with rate-limiting mass transfer. Stoichiometric ox..." @default.
- W2889608267 created "2018-09-27" @default.
- W2889608267 creator A5014484312 @default.
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- W2889608267 date "2018-09-14" @default.
- W2889608267 modified "2023-09-26" @default.
- W2889608267 title "Scalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones" @default.
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- W2889608267 doi "https://doi.org/10.1021/acs.organomet.8b00468" @default.
- W2889608267 hasPublicationYear "2018" @default.
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