Radical Cyclization of Olefinic Amides through α-C(sp3)–H Functionalization of Ketones under Catalyst-, Ligand-, and Base-Free Conditions-Reference-Cited by-同舟云学术

Radical Cyclization of Olefinic Amides through α-C(sp3)–H Functionalization of Ketones under Catalyst-, Ligand-, and Base-Free Conditions

Published:2021-03-27 Issue:09 Volume:32 Page:905-912
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Ruan Yiping¹,Liu Hongxin²,Wei Wen-Ting¹,Qin Fu-Hua¹,Kang Qing-Qing¹,Zhang Jun-Yao¹,Hu Sen-Jie¹,Liu Yi¹,Zheng Hongxing³⁴,Fang Yi-Lin⁴

Affiliation:

1. Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, School of Materials Science and Chemical Engineering, Ningbo University

2. College of Chemistry and Materials Engineering, Institute of New Materials & Industrial Technology, Wenzhou University

3. Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University

4. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University

Abstract

AbstractA new, efficient, and practical radical cyclization of olefinic amides with ketones through α-C(sp3)–H functionalization in the presence of tert-butyl peroxybenzoate (TBPB) is described for the first time. This protocol assembles a wide range of pivotal and useful benzoxazines in good to excellent yields under mild, catalyst-free, ligand-free, and base-free conditions with wide functional group tolerance. Moreover, the mechanistic study indicates that the α-carbonyl radical is involved in this transformation.

Funder

Natural Science Foundation of Zhejiang Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1468-5962.pdf

Reference1 articles.

1. Oxone-Mediated Radical Bicyclization of 1,6-Enynes through Dual α-C(sp3)–H Functionalization of Ketones under Catalyst- and Base-Free Conditions

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