Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes

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초록

We report a regioselective alkylation of quinolines enabled by activation of 1,1-diborylalkanes with organolithiums. Direct C2-alkylation occurs in THF with tert-butyllithium, whereas C4-alkylation of C2-substituted quinolines proceeds in toluene with phenyllithium. The regioselectivity arises from solvent-dependent lithium aggregation and substrate blocking of the C2-position. This protocol features a broad substrate scope and offers an alternative to multi-step alkylation sequences.

키워드

GEM-DIMETALLIC COMPOUNDSC-H FUNCTIONALIZATIONPYRIDINE N-OXIDESTERT-BUTYLLITHIUMPHENYLLITHIUMAGGREGATIONREACTIVITYEPOXIDESESTERS
제목
Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes
저자
Jo, WoohyunRyu, ChangsuYang, Jung WoonCho, Seung Hwan
DOI
10.1039/d5qo01448d
발행일
2025-12
유형
Article; Early Access
저널명
Organic Chemistry Frontiers
13
4
페이지
1292 ~ 1298