Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

Kazuhiko Semba¹, Kenta Ariyama², Hong Zheng³, Ryohei Kameyama², Shigeyoshi Sakaki⁴, Yoshiaki Nakao⁵

Affiliations

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. semba.kazuhiko.5n@kyoto-u.ac.jp.
² Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
³ Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto, 606-8103, Japan.
⁴ Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto, 606-8103, Japan. sakaki.shigeyoshi.47e@st.kyoto-u.ac.jp.
⁵ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. nakao.yoshiaki.8n@kyoto-u.ac.jp.

PMID: 27080165
DOI: 10.1002/anie.201511975

Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

Kazuhiko Semba et al. Angew Chem Int Ed Engl. 2016.

. 2016 May 17;55(21):6275-9.

doi: 10.1002/anie.201511975. Epub 2016 Apr 15.

Authors

Kazuhiko Semba¹, Kenta Ariyama², Hong Zheng³, Ryohei Kameyama², Shigeyoshi Sakaki⁴, Yoshiaki Nakao⁵

Affiliations

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. semba.kazuhiko.5n@kyoto-u.ac.jp.
² Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
³ Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto, 606-8103, Japan.
⁴ Fukui Institute for Fundamental Chemistry, Kyoto University, Sakyo-ku, Kyoto, 606-8103, Japan. sakaki.shigeyoshi.47e@st.kyoto-u.ac.jp.
⁵ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan. nakao.yoshiaki.8n@kyoto-u.ac.jp.

PMID: 27080165
DOI: 10.1002/anie.201511975

Abstract

A method for the reductive cross-coupling of conjugated arylalkenes and aryl bromides with hydrosilanes by cooperative palladium/copper catalysis was developed, thus resulting in the highly regioselective formation of various 1,1-diarylalkanes, including a biologically active molecule. Under the applied reaction conditions, high levels of functional-group tolerance were observed, and the reductive cross-coupling of internal alkynes with aryl bromides afforded trisubstituted alkenes.

Keywords: alkenes; alkynes; copper; cross-coupling; palladium.

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Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

Affiliations

Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

Authors

Affiliations

Abstract

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Full Text Sources

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