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

Woohyun Jo; Changsu Ryu; Jung Woon Yang; Seung Hwan Cho

doi:10.1039/d5qo01448d

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

Woohyun Jo^*
, Changsu Ryu
, Jung Woon Yang
, Seung Hwan Cho^*

^*Corresponding author for this work

Chemistry Education

Pohang University of Science and Technology
Sungkyunkwan University

Research output: Contribution to journal › Journal article › peer-review

1 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1292-1298
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	13
Issue number	4
DOIs	https://doi.org/10.1039/d5qo01448d
State	Published - 2026.02.17

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title = "Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes",

abstract = "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.",

author = "Woohyun Jo and Changsu Ryu and Yang, \{Jung Woon\} and Cho, \{Seung Hwan\}",

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T1 - Direct alkylation of quinolines with organolithium-activated 1,1-diborylalkanes

AU - Jo, Woohyun

AU - Ryu, Changsu

AU - Yang, Jung Woon

AU - Cho, Seung Hwan

PY - 2026/2/17

Y1 - 2026/2/17

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/105026710412

U2 - 10.1039/d5qo01448d

DO - 10.1039/d5qo01448d

M3 - Journal article

AN - SCOPUS:105026710412

SN - 2052-4110

VL - 13

SP - 1292

EP - 1298

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 4

ER -

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

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