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
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Summary:[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.
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ISSN:0021-9517
DOI:10.1016/j.jcat.2024.115460