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Synthesis 2019; 51(18): 3511-3519
DOI: 10.1055/s-0037-1611888
paper
© Georg Thieme Verlag Stuttgart · New York

KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles

Bochao Zhou
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Shiyu Guo
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Zheng Fang
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Zhao Yang
b   School of Engineering, China Pharmaceutical University, No. 639 Longmian Avenue, Nanjing 211198, P. R. of China
,
Chengkou Liu
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Wei He
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Ning Zhu
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Xin Li
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
,
Kai Guo∗
a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
c   State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China   Email: guok@njtech.edu.cn
› Author AffiliationsThis research was supported by the National Key Research and Development Program of China (2016YFB0301501), the National Natural Science Foundation of China (Grant Nos. 21776130 & 21878145), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (Nos. X1821 & X1802), the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP), and the Postgraduate Research & Practice Innovation Program of Jiangsu Province.
Further Information

Publication History

Received: 13 May 2019

Accepted after revision: 21 June 2019

Publication Date:
11 July 2019 (online)

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Abstract

A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.

Key words

styrenes - metal free - dicarbonyl indoles - synthetic methods

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611888.
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