Copper-Catalyzed Divergent1,4-Polyhaloalkylcyanationof 1,3-Enynes
Abstract We report a switchable copper-catalyzed divergent 1,4-polyhaloalkylcyanation of 1,3-enynes to construct a series of polyhalogenated allenes with high chemoselectivity and regioselectivity. The 1,4-dichloromethylcyanation of 1,3-enynes is realized by merging aminoalkyl radical-induced homolytic activation of carbon–halogen bonds with copper catalysis, while employing dtbbpy as ligands enables 1,4-trichloromethylcyanation of 1,3-enynes by hydrogen atom transfer (HAT) reactions of chloroform. Mechanistic investigations indicate that the reactions involve the selective generation of polyhalomethyl radicals by HAT or XAT process.
Authors
- Weiya Pu
- Jun‐Long Zhan (ORCID: https://orcid.org/0000-0002-2407-9513)
- Yunhe Lv (ORCID: https://orcid.org/0000-0001-5804-7475)
- Shengjun Zhang (ORCID: https://orcid.org/0000-0001-7950-5420)
- Fei Chen (ORCID: https://orcid.org/0000-0001-5145-6073)
- Rui Li (ORCID: https://orcid.org/0000-0002-5903-3996)
- Fengyu Zhang (ORCID: https://orcid.org/0000-0002-1418-0626)
- Shuhui Wang (ORCID: https://orcid.org/0000-0002-5931-0527)
- Hanshuo Chang
- Shunyu Shang
Institutions
- Anyang Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-08-14
- DOI
- https://doi.org/10.1021/acs.joc.6c01530
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Anyang Normal University