Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

Kiyofumi Inamoto; Tetsuya Yamada; Sei Ichi Kato; Shoko Kikkawa; Yoshinori Kondo

doi:10.1016/j.tet.2013.08.061

Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

Kiyofumi Inamoto, Tetsuya Yamada, Sei Ichi Kato, Shoko Kikkawa, Yoshinori Kondo

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

8 Citations (Scopus)

Abstract

The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.

Original language	English
Pages (from-to)	9192-9199
Number of pages	8
Journal	Tetrahedron
Volume	69
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2013.08.061
Publication status	Published - 2013 Nov 4
Externally published	Yes

Keywords

1,3-Dithianes
Aldehydes
Deprotection
Desulfurization
Ketones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system",

abstract = "The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.",

keywords = "1,3-Dithianes, Aldehydes, Deprotection, Desulfurization, Ketones",

author = "Kiyofumi Inamoto and Tetsuya Yamada and Kato, {Sei Ichi} and Shoko Kikkawa and Yoshinori Kondo",

note = "Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (B) (No. 23390002 ), a Grant-in-Aid for Scientific Research (C) (No. 25460002 ), and a Grant-in-Aid for Challenging Exploratory Research (No. 25670002 ) from Japan Society for the Promotion of Science , and a Grant-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Advanced Molecular Transformations by Organocatalysts{\textquoteright} (No. 23105009 ) from The Ministry of Education, Culture, Sports, Science and Technology , Japan. ",

year = "2013",

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language = "English",

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T1 - Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system

AU - Inamoto, Kiyofumi

AU - Yamada, Tetsuya

AU - Kato, Sei Ichi

AU - Kikkawa, Shoko

AU - Kondo, Yoshinori

N1 - Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (B) (No. 23390002 ), a Grant-in-Aid for Scientific Research (C) (No. 25460002 ), and a Grant-in-Aid for Challenging Exploratory Research (No. 25670002 ) from Japan Society for the Promotion of Science , and a Grant-in-Aid for Scientific Research on Innovative Areas ‘Advanced Molecular Transformations by Organocatalysts’ (No. 23105009 ) from The Ministry of Education, Culture, Sports, Science and Technology , Japan.

PY - 2013/11/4

Y1 - 2013/11/4

N2 - The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.

AB - The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.

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KW - Deprotection

KW - Desulfurization

KW - Ketones

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