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Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes

247 Pages Posted: 16 Apr 2019 Sneak Peek Status: Under Review

See all articles by Yadong Gao

Yadong Gao

Nanjing University of Science and Technology - School of Chemical Engineering; National Institute of Biological Sciences

Chao Yang

Nanjing University of Science and Technology - School of Chemical Engineering; National Institute of Biological Sciences

Jing Wang

Peking University - State Key Laboratory of Natural and Biomimetic Drugs

Chao Jiang

Nanjing University of Science and Technology - School of Chemical Engineering

Xiangbing Qi

National Institute of Biological Sciences

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Abstract

Transition-metal-catalyzed cross-coupling reactions between naturally abundant sp3-hybridized carbon centers facilitate access to diverse molecules with complex three-dimensional structures. Organometallic compounds are among one of the most powerful reagents that broadly used in carbon–carbon bonds formations. Although sp2-hybridized organometallic compounds are widely used in cross-couplings, sp3-hybridized organometallic coupling partners are less developed. Herein, we report visible-light-induced single nickel-catalyzed C(sp3)–C(sp3), C(sp3)–C(sp2), and C(sp3)–C(sp) cross-coupling reactions using alkylzirconocenes, which are easily generated in situ from terminal or internal unactivated alkenes through hydrozirconation and chain walking. This method is mild and applicable for a large range of substrates including primary, secondary, tertiary alkyl, aryl, alkenyl, alkynyl halides and a variety of alkenes. Mechanistic studies suggest a novel nickel-catalyzed radical cross-coupling pathway, which represents the first visible-light-induced transformation of alkylzirconocenes.

Keywords: cross-coupling, photocatalysis, nickel precatalyst, alkylzirconocenes, unactivated alkenes, hydrozirconation, chain walk

Suggested Citation

Gao, Yadong and Yang, Chao and Wang, Jing and Jiang, Chao and Qi, Xiangbing, Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes (April 16, 2019). Available at SSRN: https://ssrn.com/abstract=3372969 or http://dx.doi.org/10.2139/ssrn.3372969
This is a paper under consideration at Cell Press and has not been peer-reviewed.

Yadong Gao

Nanjing University of Science and Technology - School of Chemical Engineering

No.219, Ningliu Road
Nanjing, Jiangsu
China

National Institute of Biological Sciences

7 Science Park Road
ZGC Life Science Park
Beijing, 102206
China

Chao Yang

Nanjing University of Science and Technology - School of Chemical Engineering

No.219, Ningliu Road
Nanjing, Jiangsu
China

National Institute of Biological Sciences

7 Science Park Road
ZGC Life Science Park
Beijing, 102206
China

Jing Wang

Peking University - State Key Laboratory of Natural and Biomimetic Drugs

Beijing, 100191
China

Chao Jiang

Nanjing University of Science and Technology - School of Chemical Engineering ( email )

No.219, Ningliu Road
Nanjing, Jiangsu
China

Xiangbing Qi (Contact Author)

National Institute of Biological Sciences ( email )

7 Science Park Road
ZGC Life Science Park
Beijing, 102206
China

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