File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Catalytic and stoichiometrically directed synthesis of less accessible bromothiophenes and bromobithiophenes. Trapping and characterization of catalytic intermediates of trans-PdBr(C4H4-nBrn-1S-C)(PPh3)(2) (n = 1-4), trans-PdBr(C8H4BrS2-C)(PPh3)(2), and trans,trans-Pd2Br2(mu-C8H6-nBrn-2S2-C,C ')(PPh3)(4) (n = 2, 4)

TitleCatalytic and stoichiometrically directed synthesis of less accessible bromothiophenes and bromobithiophenes. Trapping and characterization of catalytic intermediates of trans-PdBr(C4H4-nBrn-1S-C)(PPh3)(2) (n = 1-4), trans-PdBr(C8H4BrS2-C)(PPh3)(2), and trans,trans-Pd2Br2(mu-C8H6-nBrn-2S2-C,C ')(PPh3)(4) (n = 2, 4)
Authors
Issue Date1998
Citation
Organometallics, 1998, v. 17, n. 18, p. 3988-3995 How to Cite?
AbstractA facile one-pot procedure for synthesizing isomerically pure bromothiophenes and bromobithiophenes was achieved by palladium-catalyzed hydrodebromination. The compounds synthesized include 2,3,4-tribromothiophene (2), 3,4-dibromothiophene (3), 2,3-dibromothiophene (7), 3-bromothiophene (4), 3,3′,5-tribromo-2,2′-bithiophene (10), 3,3′-dibromo-2,2′-bithiophene (11), and 3-bromo-2,2′-bithiophene (12). The regioselectivity is catalytically dictated by the metalation site, whereas the extent of debromination is conveniently controlled by the stoichiometry and substrate quantity. Under favorable conditions, complete debromination takes place, giving rise to thiophene and bithiophene. The catalytic intermediates trans-PdBr(3,4-C4HBr2S-C)(PPh3)2 (16), trans,trans-Pd2Br2(μ-C8H2Br 2S2-C,C′)(PPh3)4 (17), trans,trans-Pd2Br2(μ-C8H 4S2-C,C′)(PPh3)4 (18), trans-PdBr(C8H4BrS2-C)(PPh3) 2 (19), trans-PdBr(C4H3S-C)(PPh3)2 (20), and trans-PdBr(3,4,5-C4Br3S-C)(PPh3)2 (21) were isolated. Palladium insertion invariably occurs at the C(α)-Br bonds of the thiophene or bithiophene rings. Single-crystal X-ray crystallography analyses of 20, 16, and 21 gave three mononuclear square-planar Pd(II) thienyl structures with phosphines in trans orientations.
Persistent Identifierhttp://hdl.handle.net/10722/237543
ISSN
2017 Impact Factor: 4.051
2015 SCImago Journal Rankings: 2.043
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorXie, Yang-
dc.contributor.authorWu, Bo Mu-
dc.contributor.authorXue, Feng-
dc.contributor.authorNg, Siu Choon-
dc.contributor.authorMak, Thomas C W-
dc.contributor.authorAndy Hor, T. S.-
dc.date.accessioned2017-01-16T06:09:36Z-
dc.date.available2017-01-16T06:09:36Z-
dc.date.issued1998-
dc.identifier.citationOrganometallics, 1998, v. 17, n. 18, p. 3988-3995-
dc.identifier.issn0276-7333-
dc.identifier.urihttp://hdl.handle.net/10722/237543-
dc.description.abstractA facile one-pot procedure for synthesizing isomerically pure bromothiophenes and bromobithiophenes was achieved by palladium-catalyzed hydrodebromination. The compounds synthesized include 2,3,4-tribromothiophene (2), 3,4-dibromothiophene (3), 2,3-dibromothiophene (7), 3-bromothiophene (4), 3,3′,5-tribromo-2,2′-bithiophene (10), 3,3′-dibromo-2,2′-bithiophene (11), and 3-bromo-2,2′-bithiophene (12). The regioselectivity is catalytically dictated by the metalation site, whereas the extent of debromination is conveniently controlled by the stoichiometry and substrate quantity. Under favorable conditions, complete debromination takes place, giving rise to thiophene and bithiophene. The catalytic intermediates trans-PdBr(3,4-C4HBr2S-C)(PPh3)2 (16), trans,trans-Pd2Br2(μ-C8H2Br 2S2-C,C′)(PPh3)4 (17), trans,trans-Pd2Br2(μ-C8H 4S2-C,C′)(PPh3)4 (18), trans-PdBr(C8H4BrS2-C)(PPh3) 2 (19), trans-PdBr(C4H3S-C)(PPh3)2 (20), and trans-PdBr(3,4,5-C4Br3S-C)(PPh3)2 (21) were isolated. Palladium insertion invariably occurs at the C(α)-Br bonds of the thiophene or bithiophene rings. Single-crystal X-ray crystallography analyses of 20, 16, and 21 gave three mononuclear square-planar Pd(II) thienyl structures with phosphines in trans orientations.-
dc.languageeng-
dc.relation.ispartofOrganometallics-
dc.titleCatalytic and stoichiometrically directed synthesis of less accessible bromothiophenes and bromobithiophenes. Trapping and characterization of catalytic intermediates of trans-PdBr(C4H4-nBrn-1S-C)(PPh3)(2) (n = 1-4), trans-PdBr(C8H4BrS2-C)(PPh3)(2), and trans,trans-Pd2Br2(mu-C8H6-nBrn-2S2-C,C ')(PPh3)(4) (n = 2, 4)-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1021/om9800142-
dc.identifier.scopuseid_2-s2.0-0001031235-
dc.identifier.volume17-
dc.identifier.issue18-
dc.identifier.spage3988-
dc.identifier.epage3995-
dc.identifier.isiWOS:000075791000023-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats