Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-01 DOI:10.1021/acs.orglett.4c04713

Qiaojing Pan, Sihan Jia, Zi-Heng Fan, Lei Cao, Yan-Na Ma, Xuenian Chen

引用次数: 0

Abstract

Herein, we report a method for the regioselective alkylation and phosphonation of quinoline C4–H via a B₃H₇-mediated nucleophilic addition of Turbo Grignard reagents and phosphine oxide anions to quinolines bearing different substituents, affording the 4-alkyl and 4-phosphoryl quinolines and tetrahydroquinolines after one-pot oxidation or reduction. The results indicate that coordination of the B₃H₇ group can activate substrates toward a potential 1,4-dearomative addition and subtly control the regioselectivity by preventing the 1,2-dearomative addition.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.