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. 2015 Aug 7;17(15):3822-5.
doi: 10.1021/acs.orglett.5b01797. Epub 2015 Jul 16.

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System

Shoji Fujita  1 , Masanori Abe  1 , Masatoshi Shibuya  1 , Yoshihiko Yamamoto  1
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Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System

Shoji Fujita et al. Org Lett. .

Abstract

A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

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