Catalytic remodeling of complex alkenes to oxonitriles through C=C double bond deconstruction
Deconstructive transformation of carbon-carbon double bonds (C=C) is a pivotal strategy in synthetic chemistry and drug discovery. Despite the substantial advances in olefin metathesis and ozonolysis for natural product synthesis through C=C double-bond cleavage, the catalytic remodeling of complex molecules through C=C double-bond deconstruction has been underdeveloped. We report a heterogeneous copper-catalyzed C=C double-bond cleavage, which enables the remodeling of complex molecules by converting the carbons on either side of the C=C double bond to carbonyl and cyano groups, respectively. In particular, this method provides an efficient protocol to conveniently transform terpenoids, glycals, steroids, and bioactive molecules to privileged scaffolds with underexplored chemical space.
Authors
- Chenhao Li (ORCID: https://orcid.org/0009-0005-6765-0301)
- Pengfei Cao (ORCID: https://orcid.org/0000-0003-2391-1838)
- Chun-Gu Xia
- Guikai Zhang
- Xinyuan Shan (ORCID: https://orcid.org/0000-0001-5458-3975)
- Ning Jiao (ORCID: https://orcid.org/0000-0003-0290-9034)
- Kaimeng Huang
- Teng Wang (ORCID: https://orcid.org/0000-0003-2545-8619)
- Anmin Zheng (ORCID: https://orcid.org/0000-0001-7115-6510)
- Haofeng Sun (ORCID: https://orcid.org/0009-0009-7762-0009)
- Zengrui Cheng (ORCID: https://orcid.org/0000-0003-1156-2933)
- Chen Wang
- Wei Chen (ORCID: https://orcid.org/0000-0002-8955-9497)
- Lili Chen (ORCID: https://orcid.org/0009-0009-1960-4158)
- Liang Wang (ORCID: https://orcid.org/0000-0002-5826-1866)
- Song Song (ORCID: https://orcid.org/0000-0001-6679-1982)
- Min Lin (ORCID: https://orcid.org/0000-0001-8666-0568)
- Xinyao Li (ORCID: https://orcid.org/0000-0001-5230-782X)
- Ziyao Zhang (ORCID: https://orcid.org/0009-0009-8377-6173)
- Zhibin Hu (ORCID: https://orcid.org/0000-0001-6782-327X)
- Xue Jiang
- Hui Tan
- Xingtian Shu
- Zhongying Zhang (ORCID: https://orcid.org/0009-0007-9148-0212)
Institutions
- Sinopec (China) (CN)
- University of Science and Technology of China (CN)
- Shanghai University of Engineering Science (CN)
- Chinese Academy of Sciences (CN)
- Peking University (CN)
- Wuhan Institute of Physics and Mathematics (CN)
- Institute of High Energy Physics (AT)
- Institute of High Energy Physics (CN)
- Wuhan University of Science and Technology (CN)
- Beijing University of Chemical Technology (CN)
- Zhejiang University (CN)
- Wuhan Institute of Technology (CN)
Publication Details
- Journal
- Science
- Published
- 2025-03-06
- DOI
- https://doi.org/10.1126/science.adq8918
- Citations
- 27
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 25.27