A Versatile Route to Unstable Diazo Compounds via Oxadiazolines and their Use in Aryl-Alkyl Cross-Coupling Reactions

Angewandte Chemie
Andreas GrebSteven V Ley

Abstract

Coupling of readily available boronic acids and diazo compounds has emerged recently as a powerful metal-free carbon-carbon bond forming method. However, the difficulty in forming the unstable diazo compound partner in a mild fashion has hitherto limited their general use and the scope of the transformation. Here, we report the application of oxadiazolines as precursors for the generation of an unstable family of diazo compounds using flow UV photolysis and their first use in divergent protodeboronative and oxidative C(sp2 )-C(sp3 ) cross-coupling processes, with excellent functional-group tolerance.

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Citations

Aug 21, 2020·Future Medicinal Chemistry·Enol LópezJesús Alcázar
May 20, 2020·Chemistry : a European Journal·Thomas H Rehm
Mar 27, 2018·Chemistry : a European Journal·Katharina J Hock, Rene M Koenigs
Jan 25, 2019·Angewandte Chemie·Marc Montesinos-MagranerAbraham Mendoza
Sep 12, 2018·Chemical Communications : Chem Comm·Paul DingwallSteven V Ley
Jul 11, 2020·Beilstein Journal of Organic Chemistry·Jiaxi Xu
Mar 27, 2018·Angewandte Chemie·Pauline RullièreAndré B Charette
Aug 1, 2018·Organic & Biomolecular Chemistry·Marcus Baumann
Jan 21, 2021·Nature Communications·Kai YangQiuling Song
Jan 28, 2020·Organic Process Research & Development·Sebastian P GreenJames A Bull
May 7, 2021·Chemical Communications : Chem Comm·Rajdip Chowdhury, Abraham Mendoza
Nov 18, 2018·The Journal of Organic Chemistry·Yiding ChenSteven V Ley
Feb 23, 2019·Journal of Medicinal Chemistry·Andrew R Bogdan, Amanda W Dombrowski
Jun 17, 2020·The Journal of Organic Chemistry·Robert-Cristian RacleaPhilip J Parsons
Dec 22, 2020·Journal of the American Chemical Society·Yangyang YangTian Qin
Sep 16, 2021·The Journal of Organic Chemistry·Oliver M GriffithsSteven V Ley

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