Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis

doi:10.1002/cjoc.201800461

	Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis
	Liu, Mingshang1,2 ; Huang, Hanchu 1; Chen, Yiyun1,2
	2018-12
发表期刊	CHINESE JOURNAL OF CHEMISTRY (IF:5.5[JCR-2023],5.2[5-Year])
ISSN	1001-604X
卷号	36 期号:12 页码:1209-1212
发表状态	已发表
DOI	10.1002/cjoc.201800461
摘要	All-carbon quaternary centers are prevalent in bioactive small molecules. However, their efficient construction remains a formidable synthetic challenge. Here we report cyclic iodine(III) reagents enable the synthesis of cyclopentanones, cyclohexanones, and dihydrofuranones bearing alpha-quaternary centers by photoredox catalysis. The reaction proceeds by the formation of the novel cyclic iodine(III) reagent-allylic alcohol complex, which enables the first alkyl boronate addition and semi-pinacol rearrangement of allylic alcohols with dual alcohol and olefin activation. The reaction is suitable for gram scale synthesis and is transformable to alcohols, olefins, oximes, and lactones with an alpha-quaternary center in one step.
关键词	allylic alcohol cyclic iodine reagents quaternary all-carbon center photoredox catalysis alkyl boronate
收录类别	SCI ; SCIE ; IC ; CCR ; CSCD
语种	英语
资助项目	Strategic Priority Research Program of the Chinese Academy of Sciences[XDB20020200]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000450017200019
出版者	WILEY-V C H VERLAG GMBH
WOS关键词	VISIBLE-LIGHT PHOTOREDOX ; CARBON QUATERNARY STEREOCENTERS ; CONCOMITANT 1,2-ARYL MIGRATION ; TRANSITION-METAL-COMPLEXES ; ORGANIC-SYNTHESIS ; ENANTIOSELECTIVE CONSTRUCTION ; SEMIPINACOL REARRANGEMENT ; RADICAL GENERATION ; RING EXPANSION ; BOND-CLEAVAGE
原始文献类型	Article
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/28702
专题	物质科学与技术学院_博士生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.Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Bioorgan & Nat Prod Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China 2.ShanghaiTech Univ, Sch Phys Sci & Technol, 100 Haike Rd, Shanghai 201210, Peoples R China
第一作者单位	物质科学与技术学院
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, Mingshang,Huang, Hanchu,Chen, Yiyun. Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis[J]. CHINESE JOURNAL OF CHEMISTRY,2018,36(12):1209-1212.
APA	Liu, Mingshang,Huang, Hanchu,&Chen, Yiyun.(2018).Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis.CHINESE JOURNAL OF CHEMISTRY,36(12),1209-1212.
MLA	Liu, Mingshang,et al."Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis".CHINESE JOURNAL OF CHEMISTRY 36.12(2018):1209-1212.