Academic Journal
Regioselective Synthesis of Indene from 3-Aryl Propargylic gem -Dipivalates Catalyzed by N -Heterocyclic Carbene Gold(I) Complexes
| العنوان: | Regioselective Synthesis of Indene from 3-Aryl Propargylic gem -Dipivalates Catalyzed by N -Heterocyclic Carbene Gold(I) Complexes |
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| المؤلفون: | Hueber, Damien, Teci, Matthieu, Brenner, Eric, Matt, Dominique, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien |
| المساهمون: | Institut de Chimie de Strasbourg (IC), Université de Strasbourg (UNISTRA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS), ANR-11-JS07-0001,Synt-Het-Au,Synthèse d'Hétérocycles par catalyse à l'or (Au)(2011) |
| المصدر: | ISSN: 1615-4150. |
| بيانات النشر: | HAL CCSD Wiley-VCH Verlag |
| سنة النشر: | 2018 |
| مصطلحات موضوعية: | Rearrangement, Homogeneous catalysis, N-heterocyclic carbenes, Gold(I), Indenes, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.CATA]Chemical Sciences/Catalysis |
| الوصف: | International audience ; 1-Aryl-3,3-bis(pivaloyloxy)propynes can be converted in good to high yields into either 1,3-or 1,2-bis(pivaloyloxy)indenes, depending on the N-heterocyclic carbene (NHC) gold(I) hexafluoroantimonate catalyst used. Almost exclusive formation of 1,3-di(oxycarbonyl)indene derivatives was achieved with cationic gold complexes containing the embracing N,N'-1,3-bis(9-butylfluorenyl)benzimidazolylidene ligand (nBu FNHC). The regioselective issue of the reaction was rationalized by the specific spatial distribution of the steric bulk in the nBu FNHC ligand. In contrast, only modest selectivities in favor of 1,2-disubstituted indenes were observed with more classical NHC gold complexes, the best selectivity being then obtained with N,N'-1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolylidene gold chloride (SIPrAuCl) as precatalyst. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| DOI: | 10.1002/adsc.201800305 |
| الاتاحة: | https://hal.science/hal-02348174 https://hal.science/hal-02348174v1/document https://hal.science/hal-02348174v1/file/Indene%20synthesis%20nBuFNHC%20revised%20version.pdf https://doi.org/10.1002/adsc.201800305 |
| Rights: | info:eu-repo/semantics/OpenAccess |
| رقم الانضمام: | edsbas.2601412C |
| قاعدة البيانات: | BASE |
| DOI: | 10.1002/adsc.201800305 |
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