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Potassium tert-Butoxide-Catalyzed Dehydrogenative Cross-Coupling of Heteroarenes with Hydrosilanes

Toutov, Anton A. and Liu, Wen-Bo and Stoltz, Brian M. and Grubbs, Robert H. (2016) Potassium tert-Butoxide-Catalyzed Dehydrogenative Cross-Coupling of Heteroarenes with Hydrosilanes. Organic Syntheses, 93 . pp. 263-271. ISSN 0078-6209. http://resolver.caltech.edu/CaltechAUTHORS:20160919-073857486

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Abstract

A. 1-Methyl-2-(triethylsilyl)-1H-indole (2). An oven-dried 100-mL round-bottom Schlenk flask is equipped with a Teflon-coated magnetic stir bar (25 x 8 mm) and capped with a rubber septum (Note 1). The side arm of the flask is connected to Schlenk line and the flask is cooled to room temperature under vacuum and back-filled with nitrogen. Potassium tert-butoxide (1.34 g, 12.0 mmol, 0.2 equiv) is added to the flask under positive nitrogen flow (Notes 2 and 3), and then the flask is evacuated and back-filled with nitrogen three times. N-Methylindole (7.48 mL, 7.86 g, 60.0 mmol, 1.0 equiv) and triethylsilane (28.6 mL, 20.82 g, 179.5 mmol, 3.0 equiv) are added sequentially via syringe through the septum, resulting in a yellow heterogeneous mixture (Figure 1). After the septum is replaced with a glass stopper (Note 4), the reaction mixture is degassed (Note 5) and stirred at 45 ºC for 76 h (Note 6), resulting in a dark purple solution. The heating bath is removed and the reaction mixture is allowed to cool to ambient temperature (~25 ºC), then anhydrous diethyl ether (30 mL) is added slowly while stirring (Note 7).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.15227/orgsyn.093.0263DOIArticle
http://orgsyn.org/demo.aspx?prep=v93p0263PublisherArticle
ORCID:
AuthorORCID
Toutov, Anton A.0000-0002-6561-0462
Liu, Wen-Bo0000-0003-2687-557X
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2016 Organic Syntheses, Inc. Published on the web 08/26/2016. This publication is based on work supported by the NSF under the CCI Center for Selective C-H Functionalization (CHE-1205646) and under CHE-1212767. W.-B.L. wishes to thank the Shanghai Institute of Organic Chemistry (SIOC) and Prof. S.-L. You for a postdoctoral fellowship. A.A.T. is grateful to the Resnick Sustainability Institute at Caltech and to Dow Chemical for a predoctoral fellowship, and to NSERC for a PGS D fellowship. We also thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. A.A.T. and W.-B.L. contributed equally to this work.
Group:Resnick Sustainability Institute
Funders:
Funding AgencyGrant Number
NSFCHE-1205646
NSFCHE-1212767
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Resnick Sustainability InstituteUNSPECIFIED
Dow Chemical CompanyUNSPECIFIED
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Record Number:CaltechAUTHORS:20160919-073857486
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20160919-073857486
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:70413
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:28 Sep 2016 19:10
Last Modified:13 Apr 2017 23:38

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