Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C-H Bonds under Rhodium Catalysis

Masahito Murai; Ryo Okada; Atsushi Nishiyama; Kazuhiko Takai

doi:10.1021/acs.orglett.6b02134

Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C-H Bonds under Rhodium Catalysis

Masahito Murai, Ryo Okada, Atsushi Nishiyama, Kazuhiko Takai

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

40 Citations (Scopus)

Abstract

Use of a rhodium catalyst with (R)-(S)-BPPFA ligand allows efficient synthesis of sila[n]helicenes via dehydrogenative silylation of C-H bonds. By selecting the proper ligands, the current method provides the ability to prepare unsymmetrical sila[n]helicene derivatives without any oxidants. The resulting sila[6]helicene is a rare example of a five-membered ring-fused [6]helicene, which was isolated as a single pure enantiomer without substituents on the terminal benzene rings.

Original language	English
Pages (from-to)	4380-4383
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.6b02134
Publication status	Published - Sep 2 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C-H Bonds under Rhodium Catalysis",

abstract = "Use of a rhodium catalyst with (R)-(S)-BPPFA ligand allows efficient synthesis of sila[n]helicenes via dehydrogenative silylation of C-H bonds. By selecting the proper ligands, the current method provides the ability to prepare unsymmetrical sila[n]helicene derivatives without any oxidants. The resulting sila[6]helicene is a rare example of a five-membered ring-fused [6]helicene, which was isolated as a single pure enantiomer without substituents on the terminal benzene rings.",

author = "Masahito Murai and Ryo Okada and Atsushi Nishiyama and Kazuhiko Takai",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Young Scientists (B) (No. 26870389) from MEXT, Japan, the Advanced Catalytic Transformation program for Carbon utilization (ACT-C) project of the Japan Science and Technology Agency (JST), and the Mitsubishi Foundation (Research Grants in the Natural Sciences). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Murai, Masahito

AU - Okada, Ryo

AU - Nishiyama, Atsushi

AU - Takai, Kazuhiko

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Young Scientists (B) (No. 26870389) from MEXT, Japan, the Advanced Catalytic Transformation program for Carbon utilization (ACT-C) project of the Japan Science and Technology Agency (JST), and the Mitsubishi Foundation (Research Grants in the Natural Sciences). Publisher Copyright: © 2016 American Chemical Society.

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N2 - Use of a rhodium catalyst with (R)-(S)-BPPFA ligand allows efficient synthesis of sila[n]helicenes via dehydrogenative silylation of C-H bonds. By selecting the proper ligands, the current method provides the ability to prepare unsymmetrical sila[n]helicene derivatives without any oxidants. The resulting sila[6]helicene is a rare example of a five-membered ring-fused [6]helicene, which was isolated as a single pure enantiomer without substituents on the terminal benzene rings.

AB - Use of a rhodium catalyst with (R)-(S)-BPPFA ligand allows efficient synthesis of sila[n]helicenes via dehydrogenative silylation of C-H bonds. By selecting the proper ligands, the current method provides the ability to prepare unsymmetrical sila[n]helicene derivatives without any oxidants. The resulting sila[6]helicene is a rare example of a five-membered ring-fused [6]helicene, which was isolated as a single pure enantiomer without substituents on the terminal benzene rings.

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Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C-H Bonds under Rhodium Catalysis

Abstract

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