Volume 46, Issue 48 pp. 9301-9304

Communication

Alkene-Directed Regioselective Nickel-Catalyzed Cross-Coupling of Cyclic Anhydrides with Diorganozinc Reagents^†

Rebecca L. Rogers,

Rebecca L. Rogers

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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Jennifer L. Moore,

Jennifer L. Moore

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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Tomislav Rovis Prof.,

Tomislav Rovis Prof.

[email protected]

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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Rebecca L. Rogers,

Rebecca L. Rogers

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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Jennifer L. Moore,

Jennifer L. Moore

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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Tomislav Rovis Prof.,

Tomislav Rovis Prof.

[email protected]

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA, Fax: (+1) 970-491-1801

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First published: 05 December 2007

https://doi.org/10.1002/anie.200703124

Citations: 32

^†

We thank Johnson and Johnson, Merck, Eli Lilly, and Boehringer-Ingelheim for support. T.R. thanks the Monfort Family Foundation for a Monfort Professorship. T.R. is a fellow of the Alfred P. Sloan Foundation. J.L.M. thanks the NIH for a Ruth Kirchstein NRSA predoctoral fellowship.

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Graphical Abstract

The -enes have it! A resident alkene directs a nickel-catalyzed cross-coupling of cyclic anhydrides with diorganozinc reagents. Relative directing effects parallel the stability of nickel–alkene complexes, with less-hindered terminal olefins dominating over internal olefins.

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Volume46, Issue48

December 10, 2007

Pages 9301-9304

Alkene-Directed Regioselective Nickel-Catalyzed Cross-Coupling of Cyclic Anhydrides with Diorganozinc Reagents^†

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Alkene-Directed Regioselective Nickel-Catalyzed Cross-Coupling of Cyclic Anhydrides with Diorganozinc Reagents†

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Alkene-Directed Regioselective Nickel-Catalyzed Cross-Coupling of Cyclic Anhydrides with Diorganozinc Reagents^†