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Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides.
Angew Chem Int Ed Engl 2018; 57(51):16857-16860AC

Abstract

The development of a general, nickel-catalyzed alkyl-Mizoroki-Heck reaction of unactivated alkyl bromides is described. The mild reaction proceeds efficiently using a wide range of primary and secondary alkyl bromides, and examples of intermolecular cross-couplings are provided. Reaction alkene regioselectivity is significantly enhanced over prior carbocyclizations using palladium catalysis. Mechanistic investigations are consistent with a direct carbocyclization in contrast to the auto-tandem atom-transfer cyclization and halide elimination previously observed with palladium catalysis.

Authors+Show Affiliations

Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599, USA.Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC, 27599, USA.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

30358060

Citation

Kwiatkowski, Megan R., and Erik J. Alexanian. "Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides." Angewandte Chemie (International Ed. in English), vol. 57, no. 51, 2018, pp. 16857-16860.
Kwiatkowski MR, Alexanian EJ. Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides. Angew Chem Int Ed Engl. 2018;57(51):16857-16860.
Kwiatkowski, M. R., & Alexanian, E. J. (2018). Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides. Angewandte Chemie (International Ed. in English), 57(51), pp. 16857-16860. doi:10.1002/anie.201810757.
Kwiatkowski MR, Alexanian EJ. Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides. Angew Chem Int Ed Engl. 2018 12 17;57(51):16857-16860. PubMed PMID: 30358060.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-Catalyzed Mizoroki-Heck-Type Reactions of Unactivated Alkyl Bromides. AU - Kwiatkowski,Megan R, AU - Alexanian,Erik J, Y1 - 2018/11/20/ PY - 2018/09/18/received PY - 2018/10/26/pubmed PY - 2019/9/3/medline PY - 2018/10/26/entrez KW - alkyl halides KW - cross-coupling KW - nickel KW - radical reactions KW - synthetic methods SP - 16857 EP - 16860 JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. VL - 57 IS - 51 N2 - The development of a general, nickel-catalyzed alkyl-Mizoroki-Heck reaction of unactivated alkyl bromides is described. The mild reaction proceeds efficiently using a wide range of primary and secondary alkyl bromides, and examples of intermolecular cross-couplings are provided. Reaction alkene regioselectivity is significantly enhanced over prior carbocyclizations using palladium catalysis. Mechanistic investigations are consistent with a direct carbocyclization in contrast to the auto-tandem atom-transfer cyclization and halide elimination previously observed with palladium catalysis. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30358060/Nickel_Catalyzed_Mizoroki_Heck_Type_Reactions_of_Unactivated_Alkyl_Bromides_ L2 - https://doi.org/10.1002/anie.201810757 DB - PRIME DP - Unbound Medicine ER -