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      Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions

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          Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions.

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            Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.

            The complex [Cp*Ru(MeCN)3]PF6 is shown to catalyze the hydrosilylation of a wide range of alkynes. Terminal alkynes afford access to alpha-vinylsilane products with good regioselectivity. Deuterium labeling studies indicate a clean trans addition process is at work. The same complex is active in internal alkyne hydrosilylation, where absolute selectivity for the trans addition process is maintained. Several internal alkyne substrate classes, including propargylic alcohols and alpha,beta-alkynyl carbonyl compounds, allow regioselective vinylsilane formation. The tolerance of a wide range of silanes is noteworthy, including alkyl-, aryl-, alkoxy-, and halosilanes. This advantage is demonstrated in the direct synthesis of triene substrates for silicon-tethered intramolecular Diels-Alder cycloadditions.
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              Hydrosilylation

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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley
                14337851
                May 04 2015
                May 04 2015
                March 17 2015
                : 54
                : 19
                : 5632-5635
                Article
                10.1002/anie.201500372
                2efa878a-16a2-4444-aafb-7f4a103ed0c8
                © 2015

                http://doi.wiley.com/10.1002/tdm_license_1.1

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