Brønsted Acid Catalysed 1,2-Silyl Shift in Propargyl Silanes

Latvijas Universitātes 76. starptautiskā konference. Ķīmijas sekcija : tēžu krājums 2018
Mikus Puriņš, Māris Turks

Here we report the use of strong Brønsted acids such as triflic acid to activate the triple bond and promote 1,2-silyl shift in propargyl silanes. Deprotonation of the resulting allyl carbenium ion provides 2-silyl-1,3-dienes in good yields. Addition of dienophiles to silyl dienes yields Diels-Alder adducts in one pot procedure. Performing this rearrangement in liquid sulfur dioxide as a polar reaction medium, it is possible to activate the triple bond even with weak Brønsted acids such as benzoic acid.

Keywords
Propargyl silane, Bronsted acid, silyl diene, silyl indene, 1,2-silyl shift

Puriņš, M., Turks, M. Brønsted Acid Catalysed 1,2-Silyl Shift in Propargyl Silanes. In: Latvijas Universitātes 76. starptautiskā konference. Ķīmijas sekcija : tēžu krājums, Latvia, Rīga, 9-9 February, 2018. Rīga: Latvijas Universitāte, 2018, pp.44-44. ISBN 978-9934-18-305-8.

Publication language
English (en)