Iron-Facilitated Oxidative Dehydrogenative CO Bond Formation by Propargylic C
H Functionalization†
Teng Wang
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Department of Chemistry, Tianjin University, Tianjin 300072 (China)
Search for more papers by this authorWang Zhou
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Search for more papers by this authorHang Yin
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Search for more papers by this authorDr. Jun-An Ma
Department of Chemistry, Tianjin University, Tianjin 300072 (China)
Search for more papers by this authorCorresponding Author
Dr. Ning Jiao
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/njSearch for more papers by this authorTeng Wang
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Department of Chemistry, Tianjin University, Tianjin 300072 (China)
Search for more papers by this authorWang Zhou
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Search for more papers by this authorHang Yin
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
Search for more papers by this authorDr. Jun-An Ma
Department of Chemistry, Tianjin University, Tianjin 300072 (China)
Search for more papers by this authorCorresponding Author
Dr. Ning Jiao
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/nj
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd. 38, Beijing 100191 (China) http://sklnbd.bjmu.edu.cn/njSearch for more papers by this authorFinancial support from the National Basic Research Program of China (973 Program 2009CB825300), the National Science Foundation of China (No. 21172006), and Peking University are greatly appreciated. We thank Zejun Xu in this group for reproducing the results of 3 ac, 3 ib, and 6 e.
Graphical Abstract
Hot couple: Propargyl azides were coupled with carboxylic acids by an iron-catalyzed dehydrogenative CO bond formation (see scheme). This method enables propargylic C
H functionalization under mild reaction conditions and also may involve the application of the azido moiety as an assisting group in CH activation.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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