Selective deprotection of Me3Si-/Ph2P(O)-protected arylalkynes: Methyl Grignard reagent-promoted dephosphorylation of Ph2P(O)-protected alkynes

Lifen Peng; Feng Xu; Kenta Shinohara; Akihiro Orita; Junzo Otera

doi:10.1246/cl.140579

Selective deprotection of Me₃Si-/Ph₂P(O)-protected arylalkynes: Methyl Grignard reagent-promoted dephosphorylation of Ph₂P(O)-protected alkynes

Lifen Peng, Feng Xu, Kenta Shinohara, Akihiro Orita, Junzo Otera

Chemistry (Twin Cities)

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

14 Scopus citations

Abstract

A Ph₂P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me₃Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal a lkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me₃Si-/Ph₂P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethyny lenes and unsymmetrically substituted ditriazol.

Original language	English (US)
Article number	CL-140579
Pages (from-to)	1610-1612
Number of pages	3
Journal	Chemistry Letters
Volume	43
Issue number	10
DOIs	https://doi.org/10.1246/cl.140579
State	Published - 2014

Bibliographical note

Publisher Copyright:
© 2014 The Chemical Society of Japan.

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10.1246/cl.140579

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title = "Selective deprotection of Me3Si-/Ph2P(O)-protected arylalkynes: Methyl Grignard reagent-promoted dephosphorylation of Ph2P(O)-protected alkynes",

abstract = "A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal a lkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethyny lenes and unsymmetrically substituted ditriazol.",

author = "Lifen Peng and Feng Xu and Kenta Shinohara and Akihiro Orita and Junzo Otera",

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T1 - Selective deprotection of Me3Si-/Ph2P(O)-protected arylalkynes

T2 - Methyl Grignard reagent-promoted dephosphorylation of Ph2P(O)-protected alkynes

AU - Peng, Lifen

AU - Xu, Feng

AU - Shinohara, Kenta

AU - Orita, Akihiro

AU - Otera, Junzo

PY - 2014

Y1 - 2014

N2 - A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal a lkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethyny lenes and unsymmetrically substituted ditriazol.

AB - A Ph2P(O)-protected alkyne underwent dephosphorylation by treatment with MeMgBr in THF with Me3Si-protection untouched. The dephosphorylation followed by a transition-metal-catalyzed coupling of the resulting terminal a lkyne with aryl halides was carried out in a one-pot manner to afford the desired coupling product. Selective deprotection of Me3Si-/Ph2P(O)-protected alkynes enabled facile syntheses of expanded π-systems such as cyclic phenyleneethyny lenes and unsymmetrically substituted ditriazol.

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