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单电子转移金属化反应:光氧化还原/镍双催化的二级烷基 β-三氟硼酸盐酮和酯与芳基溴化物的交叉偶联反应。

Single-Electron Transmetalation: Photoredox/Nickel Dual Catalytic Cross-Coupling of Secondary Alkyl β-Trifluoroboratoketones and -esters with Aryl Bromides.

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

出版信息

Org Lett. 2016 Jun 17;18(12):2994-7. doi: 10.1021/acs.orglett.6b01357. Epub 2016 Jun 6.

Abstract

The first cross-coupling of secondary alkyl β-trifluoroboratoketones and -esters has been achieved through application of photoredox/nickel dual catalysis. Although the related β-trifluoroboratoamides have been effectively cross-coupled via Pd-catalysis, the corresponding ketones and esters had proven recalcitrant prior to this report. Reactions occur under mild conditions, and a variety of functional groups and sterically and electronically diverse reaction partners are tolerated.

摘要

通过光氧化还原/镍双催化作用,首次实现了仲烷基 β-三氟硼酸盐酮和酯的交叉偶联。尽管相关的 β-三氟硼酸盐酰胺已通过 Pd 催化有效地进行了交叉偶联,但在此之前,相应的酮和酯一直被证明难以反应。反应在温和的条件下进行,各种官能团和空间位阻和电子多样性的反应伙伴都能耐受。

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