Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0

Abstract Is it possible to ‘explore’ metal’s intrinsic property—a cohesive interaction—which naturally transform M0 into an aggregate or a particle or film for driving oxidative C–C bond formation? With this intention, reduction of [Ag(NH3)2]+ to Ag0 with concurrent oxidation of different phenols/na...

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Autores principales:	Khushboo Bhanderi, Prasanna S. Ghalsasi, Katsuya Inoue
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/8f5fa6ef13de459492a53abcf3fc5814
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spelling	oai:doaj.org-article:8f5fa6ef13de459492a53abcf3fc58142021-12-02T14:12:40ZNonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag010.1038/s41598-021-81020-12045-2322https://doaj.org/article/8f5fa6ef13de459492a53abcf3fc58142021-01-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-81020-1https://doaj.org/toc/2045-2322Abstract Is it possible to ‘explore’ metal’s intrinsic property—a cohesive interaction—which naturally transform M0 into an aggregate or a particle or film for driving oxidative C–C bond formation? With this intention, reduction of [Ag(NH3)2]+ to Ag0 with concurrent oxidation of different phenols/naphthols to biphenyls was undertaken. The work is originated during careful observation of an undergraduate experiment—Tollens’ test—where silver mirror film deposition takes place on the walls of borosilicate glass test tube. When the same reaction was carried out in polypropylene (plastic-Eppendorf) tube, we observed aggregation of Ag0 leading to floating Ag-particles but not silver film deposition. This prompted us to carry out challenging cross-coupling reaction by ONLY changing the surface of the reaction flask from glass to plastic to silicones. To our surprise, we observed good selective oxidative homo-coupling on Teflon surface while cross-coupling in Eppendorf vial. Thus, we propose that the formation of biphenyl is driven by the macroscopic growth of Ag0 into [Ag-particle] orchestrated by Ag…Ag cohesive interaction. To validate results, experiments were also performed on gram scale. More importantly, oxidation of β-naphthol carried out in quartz (chiral) tube which yielded slight enantioselective excess of BINOL. Details are discussed.Khushboo BhanderiPrasanna S. GhalsasiKatsuya InoueNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-11 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Khushboo Bhanderi Prasanna S. Ghalsasi Katsuya Inoue Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
description	Abstract Is it possible to ‘explore’ metal’s intrinsic property—a cohesive interaction—which naturally transform M0 into an aggregate or a particle or film for driving oxidative C–C bond formation? With this intention, reduction of [Ag(NH3)2]+ to Ag0 with concurrent oxidation of different phenols/naphthols to biphenyls was undertaken. The work is originated during careful observation of an undergraduate experiment—Tollens’ test—where silver mirror film deposition takes place on the walls of borosilicate glass test tube. When the same reaction was carried out in polypropylene (plastic-Eppendorf) tube, we observed aggregation of Ag0 leading to floating Ag-particles but not silver film deposition. This prompted us to carry out challenging cross-coupling reaction by ONLY changing the surface of the reaction flask from glass to plastic to silicones. To our surprise, we observed good selective oxidative homo-coupling on Teflon surface while cross-coupling in Eppendorf vial. Thus, we propose that the formation of biphenyl is driven by the macroscopic growth of Ag0 into [Ag-particle] orchestrated by Ag…Ag cohesive interaction. To validate results, experiments were also performed on gram scale. More importantly, oxidation of β-naphthol carried out in quartz (chiral) tube which yielded slight enantioselective excess of BINOL. Details are discussed.
format	article
author	Khushboo Bhanderi Prasanna S. Ghalsasi Katsuya Inoue
author_facet	Khushboo Bhanderi Prasanna S. Ghalsasi Katsuya Inoue
author_sort	Khushboo Bhanderi
title	Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
title_short	Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
title_full	Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
title_fullStr	Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
title_full_unstemmed	Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0
title_sort	nonconventional driving force for selective oxidative c–c coupling reaction due to concurrent and curious formation of ag0
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/8f5fa6ef13de459492a53abcf3fc5814
work_keys_str_mv	AT khushboobhanderi nonconventionaldrivingforceforselectiveoxidativecccouplingreactionduetoconcurrentandcuriousformationofag0 AT prasannasghalsasi nonconventionaldrivingforceforselectiveoxidativecccouplingreactionduetoconcurrentandcuriousformationofag0 AT katsuyainoue nonconventionaldrivingforceforselectiveoxidativecccouplingreactionduetoconcurrentandcuriousformationofag0
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Nonconventional driving force for selective oxidative C–C coupling reaction due to concurrent and curious formation of Ag0

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