Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes

Guoxiong Hua; John B. Henry; Yang Li; Andrew R. Mount; Alexandra M. Z. Slawin; J. Derek Woollins

doi:10.1039/b924986a

Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes

Guoxiong Hua, John B. Henry, Yang Li, Andrew R. Mount, Alexandra M. Z. Slawin, J. Derek Woollins

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

Abstract

Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(mu-Se)](2) (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in excellent yields (up to 99%). Alternatively, the 2,5-diarylselenophenes (2a and 2b) can be obtained in 70-80% yields from the reaction of arylacetylene with an equivalent of O-methyl Se-hydrogen phenylphosphonodiselenoate; the latter was derived from WR and methanol. The first X-ray structure of 2,5-diarylselenophenes is presented along with characterisation of their redox properties.

Original language	English
Pages (from-to)	1655-1660
Number of pages	6
Journal	Organic & Biomolecular Chemistry
Volume	8
Issue number	7
Early online date	5 Feb 2010
DOIs	https://doi.org/10.1039/b924986a
Publication status	Published - 7 Apr 2010

Keywords

Ray crystal-structures
P-SE heterocycles
Woollins reagent
Complexes
Reactivity
Selenium
(PHP(SE)(MU-SE))(2)
Selenophene
Cyclization
Cynamides

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This is the author's version of an article in Organic and Biomolecular Chemistry. The published version (c)Royal Society of Chemistry is available from DOI: 10.1039/B924986A
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@article{ddf32f53c0574e4386baa411f8424417,

title = "Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes",

abstract = "Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(mu-Se)](2) (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in excellent yields (up to 99%). Alternatively, the 2,5-diarylselenophenes (2a and 2b) can be obtained in 70-80% yields from the reaction of arylacetylene with an equivalent of O-methyl Se-hydrogen phenylphosphonodiselenoate; the latter was derived from WR and methanol. The first X-ray structure of 2,5-diarylselenophenes is presented along with characterisation of their redox properties.",

keywords = "Ray crystal-structures, P-SE heterocycles, Woollins reagent, Complexes, Reactivity, Selenium, (PHP(SE)(MU-SE))(2), Selenophene, Cyclization, Cynamides",

author = "Guoxiong Hua and Henry, {John B.} and Yang Li and Mount, {Andrew R.} and Slawin, {Alexandra M. Z.} and Woollins, {J. Derek}",

note = "This work is funded by the EPSRC UK",

year = "2010",

month = apr,

day = "7",

doi = "10.1039/b924986a",

language = "English",

volume = "8",

pages = "1655--1660",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes

AU - Hua, Guoxiong

AU - Henry, John B.

AU - Li, Yang

AU - Mount, Andrew R.

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

N1 - This work is funded by the EPSRC UK

PY - 2010/4/7

Y1 - 2010/4/7

N2 - Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(mu-Se)](2) (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in excellent yields (up to 99%). Alternatively, the 2,5-diarylselenophenes (2a and 2b) can be obtained in 70-80% yields from the reaction of arylacetylene with an equivalent of O-methyl Se-hydrogen phenylphosphonodiselenoate; the latter was derived from WR and methanol. The first X-ray structure of 2,5-diarylselenophenes is presented along with characterisation of their redox properties.

AB - Reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(mu-Se)](2) (Woollins' reagent, WR) with one equivalent of 1,4-diarylbutane-1,4-diones 1a-g in refluxing toluene affords the corresponding 2,5-diarylselenophenes 2a-g in excellent yields (up to 99%). Alternatively, the 2,5-diarylselenophenes (2a and 2b) can be obtained in 70-80% yields from the reaction of arylacetylene with an equivalent of O-methyl Se-hydrogen phenylphosphonodiselenoate; the latter was derived from WR and methanol. The first X-ray structure of 2,5-diarylselenophenes is presented along with characterisation of their redox properties.

KW - Ray crystal-structures

KW - P-SE heterocycles

KW - Woollins reagent

KW - Complexes

KW - Reactivity

KW - Selenium

KW - (PHP(SE)(MU-SE))(2)

KW - Selenophene

KW - Cyclization

KW - Cynamides

U2 - 10.1039/b924986a

DO - 10.1039/b924986a

M3 - Article

SN - 1477-0520

VL - 8

SP - 1655

EP - 1660

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 7

ER -

Synthesis of novel 2,5-diarylselenophenes from selenation of 1,4-diarylbutane-1,4-diones or methanol/arylacetylenes

Abstract

Keywords

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