Thiocyano-oximation of Aryl Olefins Enabled by Vitamin B12 Catalysis

doi:10.6023/cjoc202603016

Chinese Journal of Organic Chemistry

ARTICLE

维生素B₁₂催化的芳基烯烃硫氰化/肟化反应研究

左子沂^a, 吕游^b,c, 黄艳萍^a, 刘晓强^b,*, 钱宇^a,*, 杨义^a,*

^a四川轻化工大学晨光高性能氟材料创新中心绿色催化四川省高校重点实验室自贡 643000;
^b中国石油大学（北京）克拉玛依校区石油学院新疆维吾尔自治区克拉玛依 834000;
^c国家管网集团工程质量监督检验有限公司成都 610095

收稿日期:2026-03-13 修回日期:2026-04-28
基金资助:
国家自然科学基金(No. 21502131)、四川省科技厅(2023NSFSC0097)、自贡市盐都科技人才计划、四川轻化工大学652科研团队和教育部产学合作协同育人项目资助项目.

Thiocyano-oximation of Aryl Olefins Enabled by Vitamin B₁₂ Catalysis

Zuo Ziyi^a, Lv You^b,c, Huang Yanping^a, Liu Xiaoqiang^b,*, Qian Yu^a,*, Yang Yi^a,*

^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:2026-03-13 Revised:2026-04-28
Contact: ^*E-mail: yangyiyoung@163.com; 125984702@qq.com; xqliu@cupk.edu.cn
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, doi: 10.6023/cjoc202603016.

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维生素B₁₂催化的芳基烯烃硫氰化/肟化反应研究

Thiocyano-oximation of Aryl Olefins Enabled by Vitamin B₁₂ Catalysis

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维生素B12催化的芳基烯烃硫氰化/肟化反应研究