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Li Y, Liu B, Li HB, et al. Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chem Commun (Camb). 2015;51(6):1024-6doi: 10.1039/c4cc08902b.
Li, Y., Liu, B., Li, H. B., Wang, Q., & Li, J. H. (2015). Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chemical communications (Cambridge, England), 51(6), 1024-6. https://doi.org/10.1039/c4cc08902b
Li, Yang, et al. "Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration." Chemical communications (Cambridge, England) vol. 51,6 (2015): 1024-6. doi: https://doi.org/10.1039/c4cc08902b
Li Y, Liu B, Li HB, Wang Q, Li JH. Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration. Chem Commun (Camb). 2015 Jan 21;51(6):1024-6. doi: 10.1039/c4cc08902b. PMID: 25446150.
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Chem Commun (Camb). 2015 Jan 21;51(6):1024-6. doi: 10.1039/c4cc08902b.

Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp(3))-H bonds of acetonitriles involving 1,2-aryl migration.

Chemical communications (Cambridge, England)

Yang Li, Bang Liu, Hai-Bing Li, Qiuan Wang, Jin-Heng Li

Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China. [email protected].

PMID: 25446150 DOI: 10.1039/c4cc08902b

Abstract

A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp(3))-H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp(3))-H oxidative coupling with the C-C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.

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