Alkyl lithium-catalyzed benzylic C–H bond addition of alkyl pyridines to α-alkenes. Issue 34 (21st August 2020)

• Record Type: Journal Article
• Authors: Luo, Yan-Long; Liu, Yu-Feng; Guan, Bing-Tao
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 34(2020)
• Page Start: 6622
• Page End: 6626
• Publication Date: 2020-08-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01499k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The alkyl lithium catalyst successfully achieved the benzylic C–H bond addition of alkyl pyridines to α-alkenes, and displayed distinct selectivity from those of transition metal catalysts. Abstract : Brønsted base catalyzed C–C bond formation reactions have been extensively utilized as reliable, efficient, and atom economical methods in organic synthesis. However, the electrophiles were mostly limited to polar ones such as imines, carbonyl compounds, α, β-unsaturated compounds, styrenes and conjugated dienes. The use of α-alkenes as electrophiles in the C–C bond formation reactions always needs transition metal catalysts. Herein, we reported an alkyl lithium-catalyzed benzylic C–H bond addition of alkyl pyridines to α-alkenes. The alkyl lithium catalyst displayed quite different selectivity from those of transition metal catalysts.