Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

Atsushi Tahara; Yasumitsu Miyamoto; Ryuta Aoto; Keisuke Shigeta; Yuta Une; Yusuke Sunada; Yukihiro Motoyama; Hideo Nagashima

doi:10.1021/acs.organomet.5b00636

Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

Atsushi Tahara, Yasumitsu Miyamoto, Ryuta Aoto, Keisuke Shigeta, Yuta Une, Yusuke Sunada, Yukihiro Motoyama, Hideo Nagashima

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

The appropriate design of a ligand (L) in IrCl(CO)(L)₂ (4) realized the efficient synthesis of π-conjugated enamines possessing hole-transport properties. The iridium complex with electron-withdrawing phosphorus ligands catalyzed the hydrosilylation of amides to the corresponding silylhemiaminals, which were transformed to the enamines by heat or by treatment with acids. High catalytic efficiency (TON > 10,000) was achieved, which made it possible for the residual iridium in the enamine product to be below 20 ppb.

Original language	English
Pages (from-to)	4895-4907
Number of pages	13
Journal	Organometallics
Volume	34
Issue number	20
DOIs	https://doi.org/10.1021/acs.organomet.5b00636
Publication status	Published - Oct 26 2015

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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AU - Tahara, Atsushi

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AU - Aoto, Ryuta

AU - Shigeta, Keisuke

AU - Une, Yuta

AU - Sunada, Yusuke

AU - Motoyama, Yukihiro

AU - Nagashima, Hideo

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AB - The appropriate design of a ligand (L) in IrCl(CO)(L)2 (4) realized the efficient synthesis of π-conjugated enamines possessing hole-transport properties. The iridium complex with electron-withdrawing phosphorus ligands catalyzed the hydrosilylation of amides to the corresponding silylhemiaminals, which were transformed to the enamines by heat or by treatment with acids. High catalytic efficiency (TON > 10,000) was achieved, which made it possible for the residual iridium in the enamine product to be below 20 ppb.

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Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines

Abstract

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