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. doi:10.15227/orgsyn.093.0263. https://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).
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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 | ||||||||||||||
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DOI: | 10.15227/orgsyn.093.0263 | ||||||||||||||
Record Number: | CaltechAUTHORS:20160919-073857486 | ||||||||||||||
Persistent URL: | https://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: | 11 Nov 2021 04:28 |
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