Highly regioselective and stereoselective synthesis of C-Aryl glycosides via nickel-catalyzed ortho -C–H glycosylation of 8-aminoquinoline benzamides

Wei-Yu Shi, Ya-Nan Ding, Nian Zheng, Xue-Ya Gou, Zhe Zhang, Xi Chen, Yu-Yong Luan, Zhi-Jie Niu, Yong-Min Liang

Chemical Communications · 2021 · 10.1039/d1cc03589d

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Abstract

A novel and cost-effective nickel catalyzed  ortho -C Ar –H glycosylation reaction with high regioselectivity and excellent α-selectivity is described.

★ 2.0 1 rating
5 : Major extension (new functional group)
4 : Minor extension (no new functional group)
3 : Reproduced as published
2 : Reproduced with deviation ×1
1 : Did not work
: Extension failed / Inconclusive

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PhD student
07 Aug 2026
★ 2 : Reproduced with deviation

Synthesis of mannosyl chloride 2b, does not proceed with the reported -78 °C overnight, but rather at -15 to 0 °C until consumption of starting material, which is done after dropwise addition of the BCl3