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Laulhé S, Blackburn JM, Roizen JL. Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Org Lett. 2016;18(17):4440-3doi: 10.1021/acs.orglett.6b02323.
Laulhé, S., Blackburn, J. M., & Roizen, J. L. (2016). Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Organic letters, 18(17), 4440-3. https://doi.org/10.1021/acs.orglett.6b02323
Laulhé, Sébastien, et al. "Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters." Organic letters vol. 18,17 (2016): 4440-3. doi: https://doi.org/10.1021/acs.orglett.6b02323
Laulhé S, Blackburn JM, Roizen JL. Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters. Org Lett. 2016 Sep 02;18(17):4440-3. doi: 10.1021/acs.orglett.6b02323. Epub 2016 Aug 18. PMID: 27537216; PMCID: PMC5433267.
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Org Lett. 2016 Sep 02;18(17):4440-3. doi: 10.1021/acs.orglett.6b02323. Epub 2016 Aug 18.

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Organic letters

Sébastien Laulhé, J Miles Blackburn, Jennifer L Roizen

Affiliations

  1. Duke University , Department of Chemistry, Box 90346, Durham, North Carolina 27708-0354, United States.

PMID: 27537216 PMCID: PMC5433267 DOI: 10.1021/acs.orglett.6b02323

Abstract

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.

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