Ph(O) group for protection of terminal acetylenes

Xin Yang; Daisuke Matsuo; Yoshinori Suzuma; Jing Kun Fang; Feng Xu; Akihiro Orita; Junzo Otera; Shingo Kajiyama; Nagatoshi Koumura; Kohjiro Hara

doi:10.1055/s-0030-1261223

Ph(O) group for protection of terminal acetylenes

Xin Yang, Daisuke Matsuo, Yoshinori Suzuma, Jing Kun Fang, Feng Xu, Akihiro Orita, Junzo Otera, Shingo Kajiyama, Nagatoshi Koumura, Kohjiro Hara

Chemistry (Twin Cities)

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

18 Scopus citations

Abstract

A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph(O)-protected ethynes were transformed to the corresponding terminal ethynes.

Original language	English (US)
Article number	U04611ST
Pages (from-to)	2402-2406
Number of pages	5
Journal	Synlett
Issue number	16
DOIs	https://doi.org/10.1055/s-0030-1261223
State	Published - 2011

Keywords

alkynes
coupling
phosphorylation
protecting groups

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title = "Ph(O) group for protection of terminal acetylenes",

abstract = "A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph(O)-protected ethynes were transformed to the corresponding terminal ethynes.",

keywords = "alkynes, coupling, phosphorylation, protecting groups",

author = "Xin Yang and Daisuke Matsuo and Yoshinori Suzuma and Fang, {Jing Kun} and Feng Xu and Akihiro Orita and Junzo Otera and Shingo Kajiyama and Nagatoshi Koumura and Kohjiro Hara",

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T1 - Ph(O) group for protection of terminal acetylenes

AU - Yang, Xin

AU - Matsuo, Daisuke

AU - Suzuma, Yoshinori

AU - Fang, Jing Kun

AU - Xu, Feng

AU - Orita, Akihiro

AU - Otera, Junzo

AU - Kajiyama, Shingo

AU - Koumura, Nagatoshi

AU - Hara, Kohjiro

PY - 2011

Y1 - 2011

N2 - A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph(O)-protected ethynes were transformed to the corresponding terminal ethynes.

AB - A protecting group Ph(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H Ph(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph(O)-protected ethynes were transformed to the corresponding terminal ethynes.

KW - alkynes

KW - coupling

KW - phosphorylation

KW - protecting groups

UR - http://www.scopus.com/inward/record.url?scp=80053051581&partnerID=8YFLogxK

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DO - 10.1055/s-0030-1261223

M3 - Article

AN - SCOPUS:80053051581

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SP - 2402

EP - 2406

JO - Synlett

JF - Synlett

IS - 16

M1 - U04611ST

ER -

Ph(O) group for protection of terminal acetylenes

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Keywords

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