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Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes
- Jo, Woohyun;
- Ryu, Changsu;
- Yang, Jung Woon;
- Cho, Seung Hwan
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2초록
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 COMPOUNDS; C-H FUNCTIONALIZATION; PYRIDINE N-OXIDES; TERT-BUTYLLITHIUM; PHENYLLITHIUM; AGGREGATION; REACTIVITY; EPOXIDES; ESTERS
- 제목
- Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes
- 저자
- Jo, Woohyun; Ryu, Changsu; Yang, Jung Woon; Cho, Seung Hwan
- 발행일
- 2025-12
- 유형
- Article; Early Access
- 권
- 13
- 호
- 4
- 페이지
- 1292 ~ 1298