Alkynyl Tetracoordinate Borons Enabled Synthesis of α-Bromo/Chloro Ketones via Sequential 1,2-Migration and Oxidation

Yajun Yu; Yi Huang; Yuquan Han; Yuanbiao An; Zihao Zhong; Ziming Chen; Xingxing Ma; Qiuling Song

doi:10.1002/cjoc.70424

Chinese Journal of Chemistry ›› 2026, Vol. 44 ›› Issue (6) :849 -854. DOI: 10.1002/cjoc.70424

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Alkynyl Tetracoordinate Borons Enabled Synthesis of α-Bromo/Chloro Ketones via Sequential 1,2-Migration and Oxidation

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Abstract

A practical and transition-metal-free synthesis of α-bromo/chloro ketones is developed via sequential 1,2-migration and oxidation of alkynyl tetracoordinate boron species under mild conditions. This method employs readily available N-bromosuccinimide (NBS) and N-chlorosuccinimide (NCS) as halogen sources, achieving high efficiency (up to 95% yield) with operational simplicity. The reaction demonstrates broad functional group tolerance, offering a versatile platform for α-halo ketones.

Keywords

Alkynyl tetracoordinate borons / α-Bromo ketones / α-Chloro ketones / 1,2-Migration / Oxidation / N-Bromosuccinimide / N-Chlorosuccinimide / Organohalides / Synthesis design / Rearrangement

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Yajun Yu, Yi Huang, Yuquan Han, Yuanbiao An, Zihao Zhong, Ziming Chen, Xingxing Ma, Qiuling Song. Alkynyl Tetracoordinate Borons Enabled Synthesis of α-Bromo/Chloro Ketones via Sequential 1,2-Migration and Oxidation. Chinese Journal of Chemistry, 2026, 44 (6) : 849-854 DOI:10.1002/cjoc.70424