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Nickel and cobalt-catalyzed coupling of alkyl halides with alkenes via heck reactions and radical conjugate addition.
Mini Rev Med Chem 2013; 13(6):802-13MR

Abstract

Cross-coupling of alkyl halides with alkenes leading to Heck-type and addition products is summarized. The development of Heck reaction with aliphatic halides although has made significant progress in the past decade and particularly recently, it was much less explored in comparison with the aryl halides. The use of Ni- and Co-catalyzed protocols allowed efficient Heck coupling of activated and unactivated alkenes with 1°, 2° and 3° alkyl halides. In addition, radical conjugate addition to activated alkenes has become a well-established method that has led to efficient construction of many natural products. The utilization of Ni- and Co-catalyzed strategies would avoid toxic tin reagents, and therefore worth exploring. The recent development of Ni- and Co-catalyzed addition of alkyl halides to alkenes displays much improved reactivity and functional group tolerance. In this mini-review, we also attempt to overview the mechanisms that are proposed in the reactions, aiming at providing insight into the nickel and cobalt-catalyzed coupling of alkyl halides with alkenes.

Authors+Show Affiliations

Department of Chemistry, Shanghai University, 99-Shang-Da Road, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Review

Language

eng

PubMed ID

23544460

Citation

Qian, Qun, et al. "Nickel and Cobalt-catalyzed Coupling of Alkyl Halides With Alkenes Via Heck Reactions and Radical Conjugate Addition." Mini Reviews in Medicinal Chemistry, vol. 13, no. 6, 2013, pp. 802-13.
Qian Q, Zang Z, Chen Y, et al. Nickel and cobalt-catalyzed coupling of alkyl halides with alkenes via heck reactions and radical conjugate addition. Mini Rev Med Chem. 2013;13(6):802-13.
Qian, Q., Zang, Z., Chen, Y., Tong, W., & Gong, H. (2013). Nickel and cobalt-catalyzed coupling of alkyl halides with alkenes via heck reactions and radical conjugate addition. Mini Reviews in Medicinal Chemistry, 13(6), pp. 802-13.
Qian Q, et al. Nickel and Cobalt-catalyzed Coupling of Alkyl Halides With Alkenes Via Heck Reactions and Radical Conjugate Addition. Mini Rev Med Chem. 2013 May 1;13(6):802-13. PubMed PMID: 23544460.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel and cobalt-catalyzed coupling of alkyl halides with alkenes via heck reactions and radical conjugate addition. AU - Qian,Qun, AU - Zang,Zhenhua, AU - Chen,Yang, AU - Tong,Weiqi, AU - Gong,Hegui, PY - 2012/07/09/received PY - 2012/09/27/revised PY - 2013/02/11/accepted PY - 2013/4/3/entrez PY - 2013/4/3/pubmed PY - 2013/9/21/medline SP - 802 EP - 13 JF - Mini reviews in medicinal chemistry JO - Mini Rev Med Chem VL - 13 IS - 6 N2 - Cross-coupling of alkyl halides with alkenes leading to Heck-type and addition products is summarized. The development of Heck reaction with aliphatic halides although has made significant progress in the past decade and particularly recently, it was much less explored in comparison with the aryl halides. The use of Ni- and Co-catalyzed protocols allowed efficient Heck coupling of activated and unactivated alkenes with 1°, 2° and 3° alkyl halides. In addition, radical conjugate addition to activated alkenes has become a well-established method that has led to efficient construction of many natural products. The utilization of Ni- and Co-catalyzed strategies would avoid toxic tin reagents, and therefore worth exploring. The recent development of Ni- and Co-catalyzed addition of alkyl halides to alkenes displays much improved reactivity and functional group tolerance. In this mini-review, we also attempt to overview the mechanisms that are proposed in the reactions, aiming at providing insight into the nickel and cobalt-catalyzed coupling of alkyl halides with alkenes. SN - 1875-5607 UR - https://www.unboundmedicine.com/medline/citation/23544460/Nickel_and_cobalt_catalyzed_coupling_of_alkyl_halides_with_alkenes_via_heck_reactions_and_radical_conjugate_addition_ L2 - http://www.eurekaselect.com/108847/article DB - PRIME DP - Unbound Medicine ER -