Copper-catalyzed radical oxidative C(sp3)–H/C(sp3)–H cross-coupling between arylacetonitriles and benzylic compounds. Issue 48 (27th November 2020)

• Record Type: Journal Article
• Authors: Xiao, Jing; Li, Fangshao; Zhong, Ting; Wu, Xiaofang; Guo, Fengzhe; Li, Qiang; Tang, Zi-Long
• Is Part Of: Tetrahedron. Volume 76:Issue 48(2020)
• Publication Date: 2020-11-27
• Subjects: Copper-catalyzed -- Radical -- C(sp3)–H/C(sp3)–H cross-coupling -- Arylacetonitriles -- Benzylic compounds; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131621
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: For the first time, a novel copper-catalyzed direct C(sp 3 )–H/C(sp 3 )–H cross-coupling of arylacetonitriles with unactivated benzylic compounds was described, allowing various a-benzylated arylacetonitriles to be readily accessible under base-free conditions. Mechanistic investigations suggested that the reaction proceeds through radical process and the C(sp 3 )–H cleavage of arylacetonitriles probably is the rate-determining step. Graphical abstract: Image 1 Highlights: Readily available benzylic compounds were used as alkylation reagents. Good functional group compatibility. Various substituted nitriles could be synthesized via direct C(sp 3 )-H/C(sp 3 )-H oxidative radical cross-coupling reactions.