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Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers
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| dc.contributor.author |
Wellington, Kevin W
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| dc.contributor.author |
Gordon, GER
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| dc.contributor.author |
Ndlovu, LA
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| dc.contributor.author |
Steenkamp, P
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| dc.date.accessioned | 2014-01-13T07:13:46Z | |
| dc.date.available | 2014-01-13T07:13:46Z | |
| dc.date.issued | 2013-06 | |
| dc.identifier.citation | Wellington, K.W, Gordon, G.E.R, Ndlovu, L.A and Steenkamp, P. 2013. Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers. ChemCatChem, vol. 5(4), pp 1570–1577 | en_US |
| dc.identifier.issn | 1867-3880 | |
| dc.identifier.uri | http://onlinelibrary.wiley.com/doi/10.1002/cctc.201200606/abstract | |
| dc.identifier.uri | http://hdl.handle.net/10204/7131 | |
| dc.description | Copyright: 2013 Wiley. This is an ABSTRACT ONLY. The definitive version is published in ChemCatChem, vol. 5(4), pp 1570–1577 | en_US |
| dc.description.abstract | Oxidative C-S and C-C bond formation with aryl and alkyl thiols was catalyzed under mild conditions in a reaction vessel open to air at pH 4.5 in the presence of a commercial laccase (Novozym 51003 or Suberase) and a cosolvent (DMF) to afford 1,4-naphthoquinone sulfides. Although both monothiolation and dithiolation of the 1,4-naphthohydroquinone were accomplished, the latter was favored. In addition, unprecedented dimerization of monothiolated intermediates occurred through C-C coupling. These commercial laccases provide a facile and a more environmentally friendly synthetic approach to both 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers. | en_US |
| dc.language.iso | en | en_US |
| dc.publisher | Wiley Online Library | en_US |
| dc.relation.ispartofseries | Workflow;11843 | |
| dc.subject | 1,4-naphthoquinone sulfides | en_US |
| dc.subject | C-C coupling | en_US |
| dc.subject | C-S coupling | en_US |
| dc.subject | Green chemistry | en_US |
| dc.subject | Laccase | en_US |
| dc.title | Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers | en_US |
| dc.type | Article | en_US |
| dc.identifier.apacitation | Wellington, K. W., Gordon, G., Ndlovu, L., & Steenkamp, P. (2013). Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers. http://hdl.handle.net/10204/7131 | en_ZA |
| dc.identifier.chicagocitation | Wellington, Kevin W, GER Gordon, LA Ndlovu, and P Steenkamp "Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers." (2013) http://hdl.handle.net/10204/7131 | en_ZA |
| dc.identifier.vancouvercitation | Wellington KW, Gordon G, Ndlovu L, Steenkamp P. Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers. 2013; http://hdl.handle.net/10204/7131. | en_ZA |
| dc.identifier.ris | TY - Article AU - Wellington, Kevin W AU - Gordon, GER AU - Ndlovu, LA AU - Steenkamp, P AB - Oxidative C-S and C-C bond formation with aryl and alkyl thiols was catalyzed under mild conditions in a reaction vessel open to air at pH 4.5 in the presence of a commercial laccase (Novozym 51003 or Suberase) and a cosolvent (DMF) to afford 1,4-naphthoquinone sulfides. Although both monothiolation and dithiolation of the 1,4-naphthohydroquinone were accomplished, the latter was favored. In addition, unprecedented dimerization of monothiolated intermediates occurred through C-C coupling. These commercial laccases provide a facile and a more environmentally friendly synthetic approach to both 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers. DA - 2013-06 DB - ResearchSpace DP - CSIR KW - 1,4-naphthoquinone sulfides KW - C-C coupling KW - C-S coupling KW - Green chemistry KW - Laccase LK - https://researchspace.csir.co.za PY - 2013 SM - 1867-3880 T1 - Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers TI - Laccase-catalyzed C-S and C-C coupling for a one-pot synthesis of 1,4-naphthoquinone sulfides and 1,4-naphthoquinone sulfide dimers UR - http://hdl.handle.net/10204/7131 ER - | en_ZA |
