4.7 Review

Merging dearomatization with redox-neutral C(sp3)-H functionalization via hydride transfer/cyclization: recent advances and perspectives

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 18, Pages 5041-5052

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01054b

Keywords

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Funding

  1. NSFC [21978144, 21776148]
  2. Support Plan on Science and Technology for Youth Innovation of Universities in Shandong Province [2019KJM002]
  3. Talents of High Level Scientific Research Foundation [6651118009, 6631115015, 6631110309]

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This review provides a timely account of the emerging hydride transfer-involved dearomatization reaction in organic synthesis. It categorizes the reaction based on different hydride acceptors, vinylogous imines and quinone methides, which initiate the cascade hydride transfer/dearomative cyclization process to dearomatize indoles and phenols. The limitations, challenges, and future directions in this field are also discussed.
Dearomatization and direct C(sp(3))-H functionalization represent two hot research fields in organic synthesis, the merging of which is among the most challenging but appealing topics. The emerging hydride transfer-involved dearomatization reaction can achieve this goal in an efficient redox-neutral manner, and encouraging progress has been made in this area during the past decade. Herein, we would like to give a timely account of the topic, and this review is categorized according to the hydride acceptors, namely vinylogous imines and quinone methides, which initiate the cascade hydride transfer/dearomative cyclization process to dearomatize indoles and phenols, respectively. Moreover, the limitations, challenges and future directions are also pointed out.

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