Metal-free C–C bond formation via coupling of nitrile imines and boronic acids. Issue 44 (3rd October 2019)

• Record Type: Journal Article
• Authors: Livingstone, Keith; Bertrand, Sophie; Mowat, Jenna; Jamieson, Craig
• Is Part Of: Chemical science. Volume 10:Issue 44(2019)
• Page Start: 10412
• Page End: 10416
• Publication Date: 2019-10-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc03032h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Photochemical generation of nitrile imine species and subsequent reaction with boronic acid derivatives furnishes a new C–C bond without transition metal catalysis. Abstract : The challenges of developing sustainable methods of carbon–carbon bond formation remains a topic of considerable importance in synthetic chemistry. Capitalizing on the highly reactive nature of the nitrile imine 1, 3-dipole, we have developed a novel metal-free coupling of this species with aryl boronic acids. Photochemical generation of a nitrile imine intermediate and trapping with a palette of boronic acids enabled rapid and facile access to a broad library of more than 25 hydrazone derivatives in up to 92% yield, forming a carbon–carbon bond in a metal free fashion. This represents the first reported example of direct reaction between boronic acids and a 1, 3-dipole.