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Updated: Feb 21, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
I2-Catalyzed cross dehydrogenative coupling: rapid access to benzoxazinones and quinazolinones
Kaili Chen1, Biao Gao, Yanguo Shang
1Jiangsu Key Laboratory of Drug Design & Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang Road, Nanjing 210009, P. R. China. jinxinwang@cpu.edu.cn.
Abstract:
An efficient and applicable I2-catalyzed intramolecular dehydrogenative C-O/C-N coupling reaction via activating the C-H bond adjacent to the N atom has been developed to provide dozens of substituted benzoxazinones (31 examples) and quinazolinones (5 examples) in good to excellent yields (up to 98%). This one-pot methodology has significant advantages, including a metal-free process, broad substrate scope, high atom economy, and simple operation. This strategy goes through an iminium intermediate followed by nucleophilic attack to provide the desired products.
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