title: Transition metal-free intramolecular regioselective couplings of aliphatic and aromatic C-H bonds.
abstract: Cross-dehydrogenative couplings of two different C-H bonds have emerged as an attractive goal in organic synthesis. However, achieving regioselective C-H activation is a great challenge because C-H bonds are ubiquitous in organic compounds. Actually, the regioselective couplings promoted by enzymes are a common occurrence in nature. Herein, we have developed simple, efficient and general transition metal-free intramolecular couplings of alphatic and aromatic C-H bonds. The protocol uses readily available aryl triazene as the radical initiator, cheap K2S2O8 as the oxidant, and the couplings were performed well with excellent tolerance of functional groups. Interestingly, α-carbon configuration of some amino acid residues in the substrates was kept after the reactions, and the couplings for substrates with substituted phenylalanine residues exhibited complete β-carbon diastereoselectivity for induction of the chiral α-carbon. Therefore, the present study should provide a novel strategy for regioselective cross-dehydrogenative couplings of two different C-H bonds.
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.|Department of Applied Chemistry, Beijing Institute of Technology, Beijing 100081, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Tian
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
authors.forename: Haijun
authors.initials: H
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, Beijing 100081, P. R. China.
authors.forename: Changjin
authors.initials: C
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.|Department of Applied Chemistry, Beijing Institute of Technology, Beijing 100081, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Fu
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