Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion

Kohei Fuchibe; Shumpei Watanabe; Go Takao; Junji Ichikawa

doi:10.1039/C9OB00540D

Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion†

Kohei Fuchibe,^a Shumpei Watanabe,^a Go Takao^a and Junji Ichikawa

*^a

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* Corresponding authors

^a Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
E-mail: junji@chem.tsukuba.ac.jp

Abstract

The insertion of 1,1-difluoroallenes was carried out to form a C–C bond exclusively on their central carbon. o-Bromophenyl-bearing 1,1-difluoroallenes underwent intramolecular insertion in the presence of a palladium catalyst. Regioselective C–C bond formation occurred to form a six-membered carbocycle, leading to pharmaceutically and agrochemically promising difluoromethylated naphthalenes.

This article is part of the themed collections: Synthetic methodology in OBC and Fluorine Chemistry

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Article information

https://doi.org/10.1039/C9OB00540D

Submitted

05 Mar 2019

Accepted

24 Apr 2019

First published

25 Apr 2019

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Org. Biomol. Chem., 2019,17, 5047-5054

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Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion

K. Fuchibe, S. Watanabe, G. Takao and J. Ichikawa, Org. Biomol. Chem., 2019, 17, 5047

DOI: 10.1039/C9OB00540D

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Organic & Biomolecular Chemistry

Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion†

Abstract

Supplementary files

Article information

Synthesis of (difluoromethyl)naphthalenes using the ring construction strategy: C–C bond formation on the central carbon of 1,1-difluoroallenes via Pd-catalyzed insertion

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