Iron-Catalyzed Ring-Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones

Ming Hua Wang; Jing Qi Tao; Fan Yang; Hong Xin; Shu Xin Gao; Li Na Guo; Pin Gao

doi:10.1002/ajoc.202200001

Iron-Catalyzed Ring-Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones

Ming Hua Wang
, Jing Qi Tao
, Fan Yang
, Hong Xin
, Shu Xin Gao
, Li Na Guo
, Pin Gao

School of Chemistry

Xi'an Jiaotong University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

An efficient iron-catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an efficient approach to a wide range of distally allylated ketones with good functional group tolerance and high regioselectivity under redox-neutral conditions. Preliminary mechanistic study implies a radical process might be involved in this reaction.

Original language	English
Article number	e202200001
Journal	Asian Journal of Organic Chemistry
Volume	11
Issue number	2
DOIs	https://doi.org/10.1002/ajoc.202200001
State	Published - Feb 2022

Keywords

C−C bond cleavage
alkyl radical
allylation
cycloalkyl hydroperoxides
iron-catalyzed

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10.1002/ajoc.202200001

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title = "Iron-Catalyzed Ring-Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones",

abstract = "An efficient iron-catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an efficient approach to a wide range of distally allylated ketones with good functional group tolerance and high regioselectivity under redox-neutral conditions. Preliminary mechanistic study implies a radical process might be involved in this reaction.",

keywords = "C−C bond cleavage, alkyl radical, allylation, cycloalkyl hydroperoxides, iron-catalyzed",

author = "Wang, \{Ming Hua\} and Tao, \{Jing Qi\} and Fan Yang and Hong Xin and Gao, \{Shu Xin\} and Guo, \{Li Na\} and Pin Gao",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH",

year = "2022",

month = feb,

doi = "10.1002/ajoc.202200001",

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volume = "11",

journal = "Asian Journal of Organic Chemistry",

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TY - JOUR

T1 - Iron-Catalyzed Ring-Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones

AU - Wang, Ming Hua

AU - Tao, Jing Qi

AU - Yang, Fan

AU - Xin, Hong

AU - Gao, Shu Xin

AU - Guo, Li Na

AU - Gao, Pin

PY - 2022/2

Y1 - 2022/2

N2 - An efficient iron-catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an efficient approach to a wide range of distally allylated ketones with good functional group tolerance and high regioselectivity under redox-neutral conditions. Preliminary mechanistic study implies a radical process might be involved in this reaction.

AB - An efficient iron-catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an efficient approach to a wide range of distally allylated ketones with good functional group tolerance and high regioselectivity under redox-neutral conditions. Preliminary mechanistic study implies a radical process might be involved in this reaction.

KW - C−C bond cleavage

KW - alkyl radical

KW - allylation

KW - cycloalkyl hydroperoxides

KW - iron-catalyzed

UR - https://www.scopus.com/pages/publications/85123264452

U2 - 10.1002/ajoc.202200001

DO - 10.1002/ajoc.202200001

M3 - 文章

AN - SCOPUS:85123264452

SN - 2193-5807

VL - 11

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 2

M1 - e202200001

ER -

Iron-Catalyzed Ring-Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones

Abstract

Keywords

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