Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement

Qiu Shi; Zhehui Liao; Zhili Liu; Jiajia Wen; Chenguang Li; Jiamin He; Jiazhen Deng; Shan Cen; Tongxiang Cao; Jinming Zhou; Shifa Zhu

doi:10.1038/s41467-022-31920-1

Nature Communications (Jul 2022)

Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement

Qiu Shi,
Zhehui Liao,
Zhili Liu,
Jiajia Wen,
Chenguang Li,
Jiamin He,
Jiazhen Deng,
Shan Cen,
Tongxiang Cao,
Jinming Zhou,
Shifa Zhu

Affiliations

Qiu Shi: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Zhehui Liao: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Zhili Liu: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Jiajia Wen: Institute of Medicinal Biotechnology, Chinese Academy of Medical Science
Chenguang Li: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Jiamin He: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Jiazhen Deng: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Shan Cen: Institute of Medicinal Biotechnology, Chinese Academy of Medical Science
Tongxiang Cao: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology
Jinming Zhou: Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University
Shifa Zhu: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology

DOI: https://doi.org/10.1038/s41467-022-31920-1
Journal volume & issue: Vol. 13, no. 1
pp. 1 – 11

Abstract

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The dearomative functionalization of aromatic compounds represents a challenging transformation, as it typically needs to overcome a great kinetic barrier. Here, the authors disclose a weak-bond-accelerated, catalyst-free dearomative [3,3]-rearrangement of o-nitrophenyl alkyne for the divergent synthesis of benzazepines and bridged polycycloalkanones via remote oxygen transposition.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

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