Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (5): 419-438.DOI: 10.6023/A17020049 Previous Articles     Next Articles

Perspectives

金催化去芳构化反应研究进展

吴文挺a, 张立明b, 游书力a   

  1. a. 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032;
    b. 美国加州大学圣巴巴拉分校 化学与生物化学系 加利福尼亚州圣芭芭拉市 93106
  • 收稿日期:2017-02-13 出版日期:2017-05-15 发布日期:2017-04-12
  • 通讯作者: 游书力, 张立明 E-mail:slyou@sioc.ac.cn;zhang@chem.ucsb.edu
  • 基金资助:

    项目受科技部国家重点研发项目(2016YFA0202900)、国家基础研究计划(973项目2015CB856600)、国家自然科学基金委(21332009,21421091)、中国科学院战略性先导项目(XDB20000000)、中国科学院前沿科学重点研究项目(QYZDY-SSW-SLH012)和中国科学院国家外国专家局创新团队国际合作伙伴计划资助.

Recent Progress on Gold-catalyzed Dearomatization Reactions

Wu Wen-Tinga, Zhang Limingb, You Shu-Lia   

  1. a. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    b. Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106
  • Received:2017-02-13 Online:2017-05-15 Published:2017-04-12
  • Contact: 10.6023/A17020049 E-mail:slyou@sioc.ac.cn;zhang@chem.ucsb.edu
  • Supported by:

    Project supported by the National Key Research and Development Program of China (2016YFA0202900), National BasicResearch Program of China (973 Program 2015CB856600), the NSFC (21332009, 21421091), Key Research and Development Program of Bureau of Frontier Sciences and Education Chinese Academy of Sciences (QYZDY-SSW-SLH012), and the Strategic Priority Research Program of the Chinese Academyof Sciences (XDB20000000) for generous financial support.

Homogeneous gold catalysis has experienced rapid development since 2004 and generally exhibited high efficiency and good functional group tolerance. On the other hand, catalytic dearomatization reactions provide a unique and straight approach to the construction of highly functionalized molecules with diverse three-dimensional structures from simple aromatic compounds. In this perspective, recent examples on gold-catalyzed dearomatization reactions are summarized in two main categories: gold-catalyzed rearrangements and gold-catalyzed hydrofunctionalizations of alkynes and allenes. In the first category, intra- and inter- molecular dearomatization reactions were achieved via gold-catalyzed rearrangements of propargylic ester and its derivatives. Although this area is still at its early stage, several outstanding asymmetric examples have been reported by Shi and Toste. In the second category, an array of dearomatization reactions via gold-catalyzed hydrofunctionalizations of alkynes and allenes were presented. All these cases have shown great potentials for convenient and straightforward construction of spiro and/or bridged polycyclic molecules, and some of them have exhibited excellent enantioselectivity. In addition, salient features and proposed mechanisms for these two types of reactions are also described.

Key words: gold catalysis, dearomatization, asymmetric catalysis, rearrangement, hydrofunctionalization