Enantioselective C(sp2)–H borylation of diarylmethylsilanes catalyzed by chiral pyridine-dihydroisoquinoline iridium complexes

Enantioselective C(sp2)−H borylations of diarylmethylsilanes were catalyzed using iridium complexes with chiral pyridine-dihydroisoquinoline (PyDHIQ) ligands. High enantioselectivities (up to >99% ee) were observed for various substrates. A gram-scale synthesis was achieved using 1 mol% of the ca...

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Bibliographic Details
Published in:Tetrahedron 2021-01, Vol.79, p.131811, Article 131811
Main Authors: Park, Dongseong, Baek, Doohyun, Lee, Chi-Woo, Ryu, Huijeong, Park, Seungchul, Han, Woosong, Hong, Sukwon
Format: Article
Language:English
Subjects:
C(sp2)−H borylation
Diarylmethylsilane
Enantioselectivities
Pyridine-dihydroisoquinoline
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Summary:Enantioselective C(sp2)−H borylations of diarylmethylsilanes were catalyzed using iridium complexes with chiral pyridine-dihydroisoquinoline (PyDHIQ) ligands. High enantioselectivities (up to >99% ee) were observed for various substrates. A gram-scale synthesis was achieved using 1 mol% of the catalyst to afford a 91% yield of the desired chiral borylated organosilane product with >99% ee. [Display omitted] •Pyridine-dihydroisoquinoline is an efficient ligand for the Ir-catalyzed asymmetric C(sp2)−H borylation using a silane directing group in high selectivity (up to >99% ee).•A gram-scale synthesis can be realized with low catalyst and ligand loadings.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131811