Citation: Xu Xu, Guanyu Zhou, Guodong Ju, Dongjie Wang, Bao Li, Yingsheng Zhao. Rhodium(Ⅲ)-catalyzed benzo[c]azepine-1, 3(2H)-dione synthesis via tandem C–H alkylation and intermolecular amination of N-methoxylbenzamide with 3-bromo-3, 3-difluoropropene[J]. Chinese Chemical Letters, ;2022, 33(2): 847-850. doi: 10.1016/j.cclet.2021.07.070 shu

Rhodium(Ⅲ)-catalyzed benzo[c]azepine-1, 3(2H)-dione synthesis via tandem C–H alkylation and intermolecular amination of N-methoxylbenzamide with 3-bromo-3, 3-difluoropropene

Xu Xu ^{a, 1} ,
Guanyu Zhou ^{a, 1} ,
Guodong Ju ^a ,
Dongjie Wang ^a ,
Bao Li ^{b, *,} ,
Yingsheng Zhao ^{a, b, *,}

a.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical, Engineering and Materials Science, Soochow University, Suzhou 215123, China
b.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453000, China

libao@htu.edu.cn

yszhao@suda.edu.cn

Received Date: 13 June 2021
Revised Date: 26 July 2021
Accepted Date: 30 July 2021
Available Online: 4 August 2021

Figures(8)

Here, a rhodium(Ⅲ)-catalyzed benzo[c]azepine-1, 3(2H)-dione synthesis via tandem C–H alkylation and intramolecular amination of N-methoxylbenzamide with 3-bromo-3, 3-difluoropropene as the alkylation agent is reported. The substituted benzamides and protected indoles are all tolerated, yielding the corresponding products in moderate to good yields. Further study revealed those bioactive compounds such as piperic acid and a key precursor of Roflumilast all perform well, highlighting the synthetic utility of this method.
- Rhodium catalysis,
- Tandem reaction,
- Seven-membered nitrogen heterocycle
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