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Ligand-Free Pd-Catalyzed Highly Selective Arylation of Allylic Esters with Retention of the Traditional Leaving Group

Authors

  • Delin Pan,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Anjun Chen,

    1. Department of Chemistry, Shandong Normal University, Jinan 250014, China
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  • Yijin Su,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Wang Zhou,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Si Li,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Wei Jia,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Juan Xiao,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, China, Fax: (+86) 10-8280-5297
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  • Qingjian Liu Dr.,

    1. Department of Chemistry, Shandong Normal University, Jinan 250014, China
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  • Liangren Zhang Dr.,

    1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100083, 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 100083, China, Fax: (+86) 10-8280-5297
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  • Financial support from Peking University and the National Science Foundation of China (No. 20742001 and No. 20702002) is greatly appreciated.

Abstract

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What leaving group? Organic halides and allylic esters undergo efficient Pd-catalyzed Heck reactions under mild conditions in air to form a new C[BOND]C bond without elimination of the β-OAc group in the intermediate palladium complex. Instead a highly regioselective β-H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme).

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