A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

Jaeyoung Ko; Jungyeob Ham; Inho Yang; Jungwook Chin; Sang Jip Nam; Heonjoong Kang

doi:10.1016/j.tetlet.2006.07.056

A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

Jaeyoung Ko, Jungyeob Ham, Inho Yang, Jungwook Chin, Sang Jip Nam, Heonjoong Kang

Department of Chemistry & Nanoscience

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

16 Scopus citations

Abstract

A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields.

Original language	English
Pages (from-to)	7101-7106
Number of pages	6
Journal	Tetrahedron Letters
Volume	47
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.056
State	Published - 25 Sep 2006

Bibliographical note

Funding Information:
J.K., J.H., I.Y., J.C., and S.N. were supported by the BK21 program, Ministry of Education and Human Resources. This work was supported by the MarineBio 21 Program, Ministry of Maritime Affairs and Fisheries, Korea.

Keywords

Grignard reagent
Halogen lithium exchange
Hydroxylated and carboxylated aryl alkyl sulfides
Lithium aryl thiolates
Sulfur
Thioethers

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10.1016/j.tetlet.2006.07.056

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title = "A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes",

abstract = "A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields.",

keywords = "Grignard reagent, Halogen lithium exchange, Hydroxylated and carboxylated aryl alkyl sulfides, Lithium aryl thiolates, Sulfur, Thioethers",

author = "Jaeyoung Ko and Jungyeob Ham and Inho Yang and Jungwook Chin and Nam, {Sang Jip} and Heonjoong Kang",

note = "Funding Information: J.K., J.H., I.Y., J.C., and S.N. were supported by the BK21 program, Ministry of Education and Human Resources. This work was supported by the MarineBio 21 Program, Ministry of Maritime Affairs and Fisheries, Korea. ",

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T1 - A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

AU - Ko, Jaeyoung

AU - Ham, Jungyeob

AU - Yang, Inho

AU - Chin, Jungwook

AU - Nam, Sang Jip

AU - Kang, Heonjoong

N1 - Funding Information: J.K., J.H., I.Y., J.C., and S.N. were supported by the BK21 program, Ministry of Education and Human Resources. This work was supported by the MarineBio 21 Program, Ministry of Maritime Affairs and Fisheries, Korea.

PY - 2006/9/25

Y1 - 2006/9/25

N2 - A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields.

AB - A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ protection of the hydroxy or carboxylic acid group by reaction with a Grignard reagent, lithium-halogen exchange, the formation of lithium thiolates, and the nucleophilic attack of lithium thiolates on various electrophiles without isolation of the thiolates, in one vessel. This procedure required a very short reaction time (1-1.5 h) and gave the corresponding sulfides in 75-97% yields.

KW - Grignard reagent

KW - Halogen lithium exchange

KW - Hydroxylated and carboxylated aryl alkyl sulfides

KW - Lithium aryl thiolates

KW - Sulfur

KW - Thioethers

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DO - 10.1016/j.tetlet.2006.07.056

M3 - Article

AN - SCOPUS:33747762003

SN - 0040-4039

VL - 47

SP - 7101

EP - 7106

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes

Abstract

Bibliographical note

Keywords

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