Cine-Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL ACS Catalysis Pub Date : 2024-06-26 DOI:10.1021/acscatal.4c02707

Eito Moriya, Kei Muto and Junichiro Yamaguchi*,

引用次数: 0

Abstract

This manuscript describes the development of the Ni/dcype-catalyzed enolate dance/coupling reaction of alkenyl pivalates with nucleophiles, resulting in cine-substitution. Pivalates derived from 1-tetralone undergo this reaction to produce C2-functionalized dihydronaphthalenes. The direct utilization of 1-tetralone is also feasible, employing Piv₂O to generate the corresponding enol pivalate in situ. Mechanistic investigations, including stoichiometric experiments, suggest that the reaction proceeds via C–O oxidative addition, nickel 1,2-translocation, and subsequent coupling with a nucleophile.

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烯醇盐的络氨酸取代：镍催化下环烯基新戊酸酯的烯醇舞/偶联反应

本手稿介绍了镍/dcype催化的烯基新戊酸酯与亲核物的烯醇舞/偶联反应的发展情况，该反应导致了嗪取代。由 1-四氢萘酮（1-tetralone）衍生的新戊酸酯经过该反应生成 C2 功能化的二氢萘。直接利用 1-四氢萘酮也是可行的，利用 Piv2O 在原位生成相应的烯醇新戊酸酯。包括化学计量学实验在内的机理研究表明，该反应是通过 C-O 氧化加成、1,2-镍移位以及随后与亲核剂偶联进行的。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.