Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones

Shuhei Sumino; Misae Uno; Hsin Ju Huang; Yen-Ku Wu; Ilhyong Ryu

doi:10.1021/acs.orglett.7b04050

Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones

Shuhei Sumino, Misae Uno, Hsin Ju Huang, Yen-Ku Wu, Ilhyong Ryu^*

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摘要

Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO₂PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO₂I.

原文	English
頁（從 - 到）	1078-1081
頁數	4
期刊	Organic Letters
卷	20
發行號	4
DOIs	https://doi.org/10.1021/acs.orglett.7b04050
出版狀態	Published - 6 2月 2018

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abstract = "Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO2PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO2I.",

author = "Shuhei Sumino and Misae Uno and Huang, {Hsin Ju} and Yen-Ku Wu and Ilhyong Ryu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b04050",

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T1 - Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones

AU - Sumino, Shuhei

AU - Uno, Misae

AU - Huang, Hsin Ju

AU - Wu, Yen-Ku

AU - Ryu, Ilhyong

PY - 2018/2/6

Y1 - 2018/2/6

N2 - Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO2PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO2I.

AB - Alkenylation and allylation of alkyl iodides with alkenyl and allyl sulfones, respectively, took place under Pd/photoirradiation system. The initial alkyl radical, derived from a single electron transfer between Pd(0) and RI, underwent the title transformations. Pd(0) was regenerated through a reductive elimination of PhSO2PdI, which is formed by the combination of the sulfonyl radical and the palladium radical. The addition of water was effective, presumably by pushing the equilibrium through hydrolysis of PhSO2I.

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U2 - 10.1021/acs.orglett.7b04050

DO - 10.1021/acs.orglett.7b04050

M3 - Article

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AN - SCOPUS:85042182502

SN - 1523-7060

VL - 20

SP - 1078

EP - 1081

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Palladium/Light induced radical alkenylation and allylation of alkyl iodides using alkenyl and allylic sulfones

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