Copper-catalyzed stereo- and regioselective borylalkylation of silicon-tethered haloalkyl alkynes to access borylated benzosilolines

[Display omitted] •Copper-catalyzed borylalkylation of silicon-tethered haloalkyl alkynes to produce functionalized benzosiloline derivatives.•Low-cost and commercial copper salt and NHC ligand were developed as the catalsyts.•The procedure show broad substrate scope with high stereo- and regioselec...

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Published inJournal of catalysis Vol. 433; p. 115460
Main Authors Li, Shi-Nan, Zou, Li-Juan, Liu, Ji-Rong, Lu, Chen-Jie, Xu, Zheng, Ye, Fei, Li, Li, Xu, Li-Wen
Format Journal Article
LanguageEnglish
Published Elsevier Inc 01.05.2024
Subjects
alkynes
Benzosilolines
Borylakylation
Carboboration
catalytic activity
Copper catalysis
moieties
Organosilanes
regioselectivity
Borylakylation
Copper catalysis
Carboboration
Organosilanes
Benzosilolines
Online AccessGet full text
ISSN0021-9517
DOI10.1016/j.jcat.2024.115460

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Abstract [Display omitted] •Copper-catalyzed borylalkylation of silicon-tethered haloalkyl alkynes to produce functionalized benzosiloline derivatives.•Low-cost and commercial copper salt and NHC ligand were developed as the catalsyts.•The procedure show broad substrate scope with high stereo- and regioselective. An efficient and practical route for the preparation of various functionalized benzosiloline derivatives via copper-catalyzed stereo- and regioselective borylalkylation reaction has been developed. Starting from silicon-tethered haloalkyl alkynes, a series of valuable benzosiloline and 2,3-dihydro-1-sila-1H-phenalene frameworks possessing a borylated exo-vinylidene moiety were efficiently prepared, which have high synthetic utility and are difficult to obtain in other aspects.
AbstractList [Display omitted] •Copper-catalyzed borylalkylation of silicon-tethered haloalkyl alkynes to produce functionalized benzosiloline derivatives.•Low-cost and commercial copper salt and NHC ligand were developed as the catalsyts.•The procedure show broad substrate scope with high stereo- and regioselective. An efficient and practical route for the preparation of various functionalized benzosiloline derivatives via copper-catalyzed stereo- and regioselective borylalkylation reaction has been developed. Starting from silicon-tethered haloalkyl alkynes, a series of valuable benzosiloline and 2,3-dihydro-1-sila-1H-phenalene frameworks possessing a borylated exo-vinylidene moiety were efficiently prepared, which have high synthetic utility and are difficult to obtain in other aspects.
An efficient and practical route for the preparation of various functionalized benzosiloline derivatives via copper-catalyzed stereo- and regioselective borylalkylation reaction has been developed. Starting from silicon-tethered haloalkyl alkynes, a series of valuable benzosiloline and 2,3-dihydro-1-sila-1H-phenalene frameworks possessing a borylated exo-vinylidene moiety were efficiently prepared, which have high synthetic utility and are difficult to obtain in other aspects.
ArticleNumber 115460
Author Lu, Chen-Jie
Li, Li
Ye, Fei
Li, Shi-Nan
Liu, Ji-Rong
Xu, Zheng
Zou, Li-Juan
Xu, Li-Wen
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Keywords Borylakylation
Copper catalysis
Carboboration
Organosilanes
Benzosilolines
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Snippet [Display omitted] •Copper-catalyzed borylalkylation of silicon-tethered haloalkyl alkynes to produce functionalized benzosiloline derivatives.•Low-cost and...
An efficient and practical route for the preparation of various functionalized benzosiloline derivatives via copper-catalyzed stereo- and regioselective...
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SubjectTerms alkynes
Benzosilolines
Borylakylation
Carboboration
catalytic activity
Copper catalysis
moieties
Organosilanes
regioselectivity
Title Copper-catalyzed stereo- and regioselective borylalkylation of silicon-tethered haloalkyl alkynes to access borylated benzosilolines
URI https://dx.doi.org/10.1016/j.jcat.2024.115460
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