Acceleration effects of phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds

Masahito Murai, Hirotaka Takeshima, Haruka Morita, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

The current work describes the marked rate of acceleration caused by phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds. The reactivity was affected by the steric and electronic nature of the phosphine ligands. The use of the bulky and electron-rich diphosphine ligand (R)-DTBM-SEGPHOS was highly effective to yield the dehydrogenative silylation products selectively in the presence of a hydrogen acceptor. An appropriate choice of C2-symmetric chiral diphosphine ligand enables the asymmetric dehydrogenative silylation via the enantioselective desymmetrization of the C(sp3)-H bond. The unprecedented catalytic germylation of C(sp3)-H bonds with dehydrogenation was also examined with the combination of the rhodium complex and a wide bite angle diphosphine ligand to provide the corresponding 2,3-dihydrobenzo[b]germoles in good yield.

Original languageEnglish
Pages (from-to)5407-5414
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
Publication statusPublished - Jun 5 2015

ASJC Scopus subject areas

  • Organic Chemistry

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