Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)2 and CHI3 under Ambient Conditions

Kyoka Sakamoto; Kazunori Miyamoto; Masataka Kubota; Tadafumi Matsunaga; Shinichiro Kamino; Masanobu Uchiyama

doi:10.1021/acs.orglett.5c00924

Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)₂ and CHI₃ under Ambient Conditions

Kyoka Sakamoto
, Kazunori Miyamoto
, Masataka Kubota
, Tadafumi Matsunaga
, Shinichiro Kamino
, Masanobu Uchiyama

School of Pharmaceutical Sciences

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

3 Citations (Scopus)

Abstract

We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.

Original language	English
Pages (from-to)	4469-4473
Number of pages	5
Journal	Organic Letters
Volume	27
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.5c00924
Publication status	Published - 2025 May 2

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c00924

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title = "Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)2 and CHI3 under Ambient Conditions",

abstract = "We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.",

author = "Kyoka Sakamoto and Kazunori Miyamoto and Masataka Kubota and Tadafumi Matsunaga and Shinichiro Kamino and Masanobu Uchiyama",

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T1 - Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)2 and CHI3 under Ambient Conditions

AU - Sakamoto, Kyoka

AU - Miyamoto, Kazunori

AU - Kubota, Masataka

AU - Matsunaga, Tadafumi

AU - Kamino, Shinichiro

AU - Uchiyama, Masanobu

PY - 2025/5/2

Y1 - 2025/5/2

N2 - We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.

AB - We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.

UR - https://www.scopus.com/pages/publications/105004012260

UR - https://www.scopus.com/pages/publications/105004012260#tab=citedBy

U2 - 10.1021/acs.orglett.5c00924

DO - 10.1021/acs.orglett.5c00924

M3 - Article

C2 - 40257930

AN - SCOPUS:105004012260

SN - 1523-7060

VL - 27

SP - 4469

EP - 4473

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)₂ and CHI₃ under Ambient Conditions

Abstract

ASJC Scopus subject areas

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