Enantioselective C(sp2)–H borylation of diarylmethylsilanes catalyzed by chiral pyridine-dihydroisoquinoline iridium complexes. (22nd January 2021)

• Record Type: Journal Article
• Authors: Park, Dongseong; Baek, Doohyun; Lee, Chi-Woo; Ryu, Huijeong; Park, Seungchul; Han, Woosong; Hong, Sukwon
• Is Part Of: Tetrahedron. Volume 79(2021)
• Publication Date: 2021-01-22
• Subjects: Pyridine-dihydroisoquinoline -- C(sp2)−H borylation -- Diarylmethylsilane -- Enantioselectivities; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131811
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Enantioselective C(sp 2 )−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. Graphical abstract: Image 1 Highlights: 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.