Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates

Abstract A new synthetic protocol for the preparation of 3-aryl-3-methoxycarbonyl cyclopropenes with an unsubstituted double bond has been developed that allowed for expanded substrate scope and improved product yields. The method involves Rh(II)-catalyzed transfer of carbenoids generated from unpur...

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Autores principales:	Rubin, M. A., Рубин, М. А.
Formato:	Статья
Lenguaje:	English
Publicado:	Elsevier Ltd 2018
Materias:	Acetylenes Cyclopropenation Cyclopropenes Diazoesters Rhodium
Acceso en línea:	https://www.scopus.com/record/display.uri?eid=2-s2.0-84937761172&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=fe656e0c7517dbc25228b3d577bd000c&sot=afnl&sdt=cl&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=31&citeCnt=11&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/3718
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spelling	ir-20.500.12258-37182020-09-14T14:16:10Z Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates Rubin, M. A. Рубин, М. А. Acetylenes Cyclopropenation Cyclopropenes Diazoesters Rhodium Abstract A new synthetic protocol for the preparation of 3-aryl-3-methoxycarbonyl cyclopropenes with an unsubstituted double bond has been developed that allowed for expanded substrate scope and improved product yields. The method involves Rh(II)-catalyzed transfer of carbenoids generated from unpurified aryldiazoesters, followed by desilylation, and is compatible with a wide range of aryldiazoesters. The employed continuous extraction of hardly soluble crude diazoesters helps avoid laborious and often cost-prohibitive isolation and purification of sensitive diazoester precursors 2018-12-19T13:01:48Z 2018-12-19T13:01:48Z 2015 Статья Edwards, A., Rubin, M. Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates // Tetrahedron. - 2015. - Volume 71. - Issue 21. - Номер статьи 26602. - Pages 3237-3246 https://www.scopus.com/record/display.uri?eid=2-s2.0-84937761172&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=fe656e0c7517dbc25228b3d577bd000c&sot=afnl&sdt=cl&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=31&citeCnt=11&searchTerm= http://hdl.handle.net/20.500.12258/3718 en Tetrahedron application/pdf application/pdf Elsevier Ltd
institution	СКФУ
collection	Репозиторий
language	English
topic	Acetylenes Cyclopropenation Cyclopropenes Diazoesters Rhodium
spellingShingle	Acetylenes Cyclopropenation Cyclopropenes Diazoesters Rhodium Rubin, M. A. Рубин, М. А. Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
description	Abstract A new synthetic protocol for the preparation of 3-aryl-3-methoxycarbonyl cyclopropenes with an unsubstituted double bond has been developed that allowed for expanded substrate scope and improved product yields. The method involves Rh(II)-catalyzed transfer of carbenoids generated from unpurified aryldiazoesters, followed by desilylation, and is compatible with a wide range of aryldiazoesters. The employed continuous extraction of hardly soluble crude diazoesters helps avoid laborious and often cost-prohibitive isolation and purification of sensitive diazoester precursors
format	Статья
author	Rubin, M. A. Рубин, М. А.
author_facet	Rubin, M. A. Рубин, М. А.
author_sort	Rubin, M. A.
title	Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
title_short	Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
title_full	Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
title_fullStr	Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
title_full_unstemmed	Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
title_sort	synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a rh(ii)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates
publisher	Elsevier Ltd
publishDate	2018
url	https://www.scopus.com/record/display.uri?eid=2-s2.0-84937761172&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=fe656e0c7517dbc25228b3d577bd000c&sot=afnl&sdt=cl&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&relpos=31&citeCnt=11&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/3718
work_keys_str_mv	AT rubinma synthesisof1arylcycloprop2enecarboxylateswithnonsubstituteddoublebondviaarhiicatalyzedcyclopropenationoftrimethylsilylacetylenewithcoarselypurifiedaryldiazoacetates AT rubinma synthesisof1arylcycloprop2enecarboxylateswithnonsubstituteddoublebondviaarhiicatalyzedcyclopropenationoftrimethylsilylacetylenewithcoarselypurifiedaryldiazoacetates
_version_	1760601785597165568

Synthesis of 1-arylcycloprop-2-ene carboxylates with non-substituted double bond via a Rh(II)-catalyzed cyclopropenation of trimethylsilylacetylene with coarsely purified aryldiazoacetates

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