A Palladium-Catalyzed Oxidative Cycloaromatization of Biaryls with Alkynes Using Molecular Oxygen as the Oxidant

Authors

  • Zhuangzhi Shi,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China), Fax: (+86) 10-8280-5297
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  • Shengtao Ding,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China), Fax: (+86) 10-8280-5297
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  • Yuxin Cui Dr.,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China), Fax: (+86) 10-8280-5297
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  • Ning Jiao Dr.

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China), Fax: (+86) 10-8280-5297
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
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  • Financial support from Peking University, the National Science Foundation of China (grant nos. 20702002, 20872003), and the National Basic Research Program of China (973 Program; grant no. 2009CB825300) is greatly appreciated. We thank Meng Su for reproducing the results of 3 ma and 3 oa in Scheme 2.

Abstract

original image

Dual activation of C[BOND]H bonds has enabled the preparation of polycyclic aromatics from arylindoles and arylbenzofurans in the absence of a directing group, and with using O2 as the oxidant (see scheme). Synthetically and medicinally important polycyclic aromatics have been easily prepared, and some of the resulting polycyclic heteroaromatics exhibit intense fluorescence.

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