Platinum complexes of aromatic selenolates

Amy Fuller; Fergus Ross Knight; Alexandra Martha Zoya Slawin; J Derek Woollins

doi:10.1002/ejic.201000357

Platinum complexes of aromatic selenolates

Amy Fuller, Fergus Ross Knight, Alexandra Martha Zoya Slawin, J Derek Woollins

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

Abstract

Several synthetic methods are used to prepare naphthalene-based aromatic 1,2-diselenoles. A new one-pot synthesis starting from naphthalene is used to produce theknown compound naphtho[1,8-c,d][1,2]diselenole (Se₂naph).Friedel–Crafts alkylation is used on Se₂naph to substitute either one tert-butyl group to form 2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se₂naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho[1,8-c,d][1,2]diselenole (dt-Se₂naph). Bromination of mt-Se₂naph results in dibromination of the naphthalene ring, rather than reaction at selenium, to give 4,7-dibromo-2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se₂naphBr₂). Reduction of the Se–Se bond in Se₂naph, mt-Se₂naph, dibenzo[c,e][1,2]diselenine (dibenzSe₂), or diphenyl diselenide (Se₂Ph₂) with LiBEt₃H, followed by in-situ addition of [PtCl₂{P(OPh)₃}₂] yields the four-coordinate mono- and dinuclear platinum(II) bis(phosphite) complexes [Pt(Se₂naph){P(OPh)₃}₂] (1), [Pt(mt-Se₂naph){P(OPh)₃}₂] (2), [Pt₂(dibenzSe₂)₂{P(OPh)₃}₂] (3), cis-[Pt(SePh)₂{P(OPh)₃}₂] (4), and trans-[Pt₂(SePh)₄{P(OPh)₃}₂] (5).

Original language	English
Pages (from-to)	4034-4043
Number of pages	10
Journal	European Journal of Inorganic Chemistry
Volume	2010
Issue number	25
DOIs	https://doi.org/10.1002/ejic.201000357
Publication status	Published - Sept 2010

Keywords

Platinum
Selenium
Heterocycles
Polyaromatic hydrocarbon ligands
Crystal-structure
Naphthalenes
TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM
Sulfur

Access to Document

10.1002/ejic.201000357

Afterrefereesderek
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1002/ejic.201000357
Accepted author manuscript, 856 KB

Cite this

@article{31de36f4270b4f1395af7504ef790f62,

title = "Platinum complexes of aromatic selenolates",

abstract = "Several synthetic methods are used to prepare naphthalene-based aromatic 1,2-diselenoles. A new one-pot synthesis starting from naphthalene is used to produce theknown compound naphtho[1,8-c,d][1,2]diselenole (Se2naph).Friedel–Crafts alkylation is used on Se2naph to substitute either one tert-butyl group to form 2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho[1,8-c,d][1,2]diselenole (dt-Se2naph). Bromination of mt-Se2naph results in dibromination of the naphthalene ring, rather than reaction at selenium, to give 4,7-dibromo-2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naphBr2). Reduction of the Se–Se bond in Se2naph, mt-Se2naph, dibenzo[c,e][1,2]diselenine (dibenzSe2), or diphenyl diselenide (Se2Ph2) with LiBEt3 H, followed by in-situ addition of [PtCl2{P(OPh)3}2] yields the four-coordinate mono- and dinuclear platinum(II) bis(phosphite) complexes [Pt(Se2naph){P(OPh)3}2] (1), [Pt(mt-Se2naph){P(OPh)3}2] (2), [Pt2(dibenzSe2)2{P(OPh)3}2] (3), cis-[Pt(SePh)2{P(OPh)3}2] (4), and trans-[Pt2(SePh)4{P(OPh)3}2] (5).",

keywords = "Platinum, Selenium, Heterocycles, Polyaromatic hydrocarbon ligands, Crystal-structure, Naphthalenes, TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM, Sulfur",

author = "Amy Fuller and Knight, {Fergus Ross} and Slawin, {Alexandra Martha Zoya} and Woollins, {J Derek}",

year = "2010",

month = sep,

doi = "10.1002/ejic.201000357",

language = "English",

volume = "2010",

pages = "4034--4043",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley-Blackwell",

number = "25",

}

TY - JOUR

T1 - Platinum complexes of aromatic selenolates

AU - Fuller, Amy

AU - Knight, Fergus Ross

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

PY - 2010/9

Y1 - 2010/9

N2 - Several synthetic methods are used to prepare naphthalene-based aromatic 1,2-diselenoles. A new one-pot synthesis starting from naphthalene is used to produce theknown compound naphtho[1,8-c,d][1,2]diselenole (Se2naph).Friedel–Crafts alkylation is used on Se2naph to substitute either one tert-butyl group to form 2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho[1,8-c,d][1,2]diselenole (dt-Se2naph). Bromination of mt-Se2naph results in dibromination of the naphthalene ring, rather than reaction at selenium, to give 4,7-dibromo-2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naphBr2). Reduction of the Se–Se bond in Se2naph, mt-Se2naph, dibenzo[c,e][1,2]diselenine (dibenzSe2), or diphenyl diselenide (Se2Ph2) with LiBEt3 H, followed by in-situ addition of [PtCl2{P(OPh)3}2] yields the four-coordinate mono- and dinuclear platinum(II) bis(phosphite) complexes [Pt(Se2naph){P(OPh)3}2] (1), [Pt(mt-Se2naph){P(OPh)3}2] (2), [Pt2(dibenzSe2)2{P(OPh)3}2] (3), cis-[Pt(SePh)2{P(OPh)3}2] (4), and trans-[Pt2(SePh)4{P(OPh)3}2] (5).

AB - Several synthetic methods are used to prepare naphthalene-based aromatic 1,2-diselenoles. A new one-pot synthesis starting from naphthalene is used to produce theknown compound naphtho[1,8-c,d][1,2]diselenole (Se2naph).Friedel–Crafts alkylation is used on Se2naph to substitute either one tert-butyl group to form 2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho[1,8-c,d][1,2]diselenole (dt-Se2naph). Bromination of mt-Se2naph results in dibromination of the naphthalene ring, rather than reaction at selenium, to give 4,7-dibromo-2-tert-butylnaphtho[1,8-c,d][1,2]diselenole (mt-Se2naphBr2). Reduction of the Se–Se bond in Se2naph, mt-Se2naph, dibenzo[c,e][1,2]diselenine (dibenzSe2), or diphenyl diselenide (Se2Ph2) with LiBEt3 H, followed by in-situ addition of [PtCl2{P(OPh)3}2] yields the four-coordinate mono- and dinuclear platinum(II) bis(phosphite) complexes [Pt(Se2naph){P(OPh)3}2] (1), [Pt(mt-Se2naph){P(OPh)3}2] (2), [Pt2(dibenzSe2)2{P(OPh)3}2] (3), cis-[Pt(SePh)2{P(OPh)3}2] (4), and trans-[Pt2(SePh)4{P(OPh)3}2] (5).

KW - Platinum

KW - Selenium

KW - Heterocycles

KW - Polyaromatic hydrocarbon ligands

KW - Crystal-structure

KW - Naphthalenes

KW - TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM

KW - Sulfur

U2 - 10.1002/ejic.201000357

DO - 10.1002/ejic.201000357

M3 - Article

SN - 1434-1948

VL - 2010

SP - 4034

EP - 4043

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 25

ER -

Platinum complexes of aromatic selenolates

Abstract

Keywords

Access to Document

Fingerprint

Cite this