Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis

doi:10.1002/anie.202213686

	Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis
	Liu, Dan 1; Yang, Kai 4; Fang, Di 1; Li, Shi-Jun 4; Lan, Yu 4,5; Chen, Yiyun1,2,3
	2023-01-02
发表期刊	ANGEWANDTE CHEMIE - INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN	1433-7851
EISSN	1521-3773
卷号	62 期号:1
发表状态	已发表
DOI	10.1002/anie.202213686
摘要	The aldehydes installation by radical formylation constitutes an attractive synthetic strategy. However, the generation of formyl radicals for organic synthesis applications remains unknown. Herein we report the first formyl radical generation from α-chloro N-methoxyphthalimides, which selectively synthesize aldehydes by alkene hydroformylation under mild photoredox conditions. The aldehydes can be installed on acrylates, acrylamides, vinyl sulfones, vinyl ketones, and complex steroids by radical hydroformylation in excellent chemoselectivity and regioselectivity. The concerted hydrochloride elimination for the formyl radical generation from α-chloro methoxy radicals is established by experimental and computational approaches. © 2022 Wiley-VCH GmbH.
关键词	Hydroformylation Ketones Acrylamides Alkoxy radicals Condition Density-functional calculations Formyl radicals Formylation Organic synthesis Radical generation Synthetic strategies Vinyl sulfones
收录类别	EI ; SCOPUS
语种	英语
出版者	John Wiley and Sons Inc
EI入藏号	20224913216205
EI主题词	Aldehydes
EI分类号	802.3 Chemical Operations ; 804.1 Organic Compounds
原始文献类型	Article in Press
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/256361
专题	物质科学与技术学院_特聘教授组_陈以昀组
通讯作者	Chen, Yiyun
作者单位	1.State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai; 200032, China; 2.School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai; 201210, China; 3.School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou; 310024, China; 4.Green Catalysis Center, College of Chemistry, Zhengzhou University, Henan, Zhengzhou; 450001, China; 5.School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing; 400030, China
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Liu, Dan,Yang, Kai,Fang, Di,et al. Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis[J]. ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,2023,62(1).
APA	Liu, Dan,Yang, Kai,Fang, Di,Li, Shi-Jun,Lan, Yu,&Chen, Yiyun.(2023).Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis.ANGEWANDTE CHEMIE - INTERNATIONAL EDITION,62(1).
MLA	Liu, Dan,et al."Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis".ANGEWANDTE CHEMIE - INTERNATIONAL EDITION 62.1(2023).