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Chinese Journal of Organic Chemistry >

0 603016 - 603016

DOI: https://doi.org/10.6023/cjoc202603016

ARTICLE

Thiocyano-oximation of Aryl Olefins Enabled by Vitamin B12 Catalysis

  • Zuo Ziyi ,
  • Lv You ,
  • Huang Yanping ,
  • Liu Xiaoqiang ,
  • Qian Yu ,
  • Yang Yi
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  • aInnovation Center for Chenguang High Performance Fluorine Material, Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science and Engineering, Zigong, Sichuan 643000;
    bSchool of Petroleum, China University of Petroleum-Beijing at Karamay, Karamay, Xinjiang 834000;
    cPipeChina Engineering Quality Supervision and Inspection Company, Chengdu, Sichuan 610095

Received date: 2026-03-13

  Revised date: 2026-04-28

  Online published: 2026-06-11

Supported by

National Natural Science Foundation of China (No. 21502131), Science & Technology Department of Sichuan Province (2023NSFSC0097), Zigong Talent Program, Scientific Research and Innovation Team Program of Sichuan University of Science and Engineering (SUSE652A007) and Industry-University Collaborative Project of the Ministry of Education.

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Abstract

Achieving high sustainability stands as an ideal goal in modern organic synthesis. Vitamin B12, as a sustainable organocobalt coenzyme crafted by the nature, has continuously advanced the innovations of eco-friendly synthetic methodologies over recent years. Here we report our endeavors in this direction for the development of vitamin B12 catalyzed thiocyano-oximation of aryl olefins. This synthetic method highlights the tandem and regioselective stitching of medicinally-privileged dense heteroatom motifs SCN and =NOH across the aryl olefins. The high reaction-site selectivity of aryl olefins over aliphatic alkenes was achieved by capitalizing radical polarity match and the tailored reversible radical carriers of vitamin B12. The usefulness of this protocol is further demonstrated by the gram-scale synthetic applicability and late-stage functionalization of several complex and value-added olefinic molecules.

Key words： Thiocyano-oximation; Aryl Olefins; Vitamin B12; Sustainable Catalysis; Radical Reaction

Cite this article

Zuo Ziyi , Lv You , Huang Yanping , Liu Xiaoqiang , Qian Yu , Yang Yi . Thiocyano-oximation of Aryl Olefins Enabled by Vitamin B12 Catalysis[J]. Chinese Journal of Organic Chemistry, 0 : 603016 -603016 . DOI: 10.6023/cjoc202603016

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