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Efficient Generation and Synthetic Applications of Alkyl-Substituted Siloxycarbenes: Suppression of Norrish-type Fragmentations of Alkanoylsilanes by Triplet Energy Transfer.

07:00 EST 8th November 2019 | BioPortfolio

Summary of "Efficient Generation and Synthetic Applications of Alkyl-Substituted Siloxycarbenes: Suppression of Norrish-type Fragmentations of Alkanoylsilanes by Triplet Energy Transfer."

Acylsilanes have been known to undergo isomerization to siloxycarbenes under photoirradiation and thus-generated carbenes can be utilized for various synthetic reactions. But this carbene formation is not necessarily efficient with some kinds of alkanoylsilanes because Norrish-type fragmentations compete, which limit synthetic utility of alkanoylsilanes as carbene precursors. In this study, generation of siloxycarbenes from alkanoylsilanes by visible-light-induced energy transfer was examined by using an Ir complex, [Ir{dF(CF 3 )ppy} 2 (dtbpy)]PF 6 , and was successfully applied to the C-C coupling reactions with boronic esters or aldehydes. This methodology efficiently suppressed undesired Norrish-type reactions and broadened synthetic utility of alkanoylsilanes.

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Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
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