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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 7: 2000 - 2014

DOI: https://doi.org/10.6023/cjoc202202028

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Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization

  • Yazhou Wang ,
  • Yuhang Zhu ,
  • Lixia Xu ,
  • Rui He ,
  • Jian Zhang
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  • aChunliang Oil Prod Plant, Shengli Oilfield, China Petro-Chemical Corporation, Binzhou, Shandong 256600
    bCollege of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121
    cDepartment of Stomatology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou 310015
* E-mail: ;

Received date: 2022-02-23

  Revised date: 2022-03-23

  Online published: 2022-04-11

Supported by

Natural Science Foundation of Zhejiang Province(LY19B020006); Key Subject of Stomatology in Hangzhou City

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Abstract

Vicinal group-directed alkenyl C—H functionalization provides general method toward the synthesis of multi- substituted alkenes, proceeding by the weakly coordination-group (such as hydroxyl, amide, carboxylic acid, amino group etc.) assisted endo-cyclometallation, leading to vicinal C—H functionalization with excellent E/Z selectivities, including alkenylation, alkylation, arylation, alkynylation, allylation, domino cyclization etc. In stark contrast, geminal group-directed alkenyl C—H functionalization attracted much less attentions presumably due to the difficult formation of exo-metallocyles, which greatly inhibited the development of directed alkenyl C—H functionalization. In recent years, several groups have demonstrated the importance of geminal group-directed alkenyl C—H functionalization, including alkenylation, arylation, alkynylation, allylation and iodination. The research progress is introduced according to the types of geminal C—H functionalization, and the reaction mechanisms and applications of specific reactions are discussed. The development prospects with outlook are also summarized

Key words： transition-metal-catalysis; alkenes; directing group; geminal; vicinal; C—H functionalization

Cite this article

Yazhou Wang , Yuhang Zhu , Lixia Xu , Rui He , Jian Zhang . Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2000 -2014 . DOI: 10.6023/cjoc202202028

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