Development of Oxidative Formylation and Ketonylation Reactions

Abstract

The first oxidative formylation and oxidative ketonylation of alkenylamines and alkenyl alcohols is demonstrated. A range of substrates that participate in this process are provided. Oxidative formylation was found to proceed optimally with the use of triphenylsilane as the hydride source. Oxidative ketonylation was feasible with a number of organometallic partners, especially dialkylzinc or organostannanes. An interesting finding regarding the fate of various acylpalladium intermediates is discussed.

Key words

oxidative carbonylation - palladium - multicomponent reaction - formylation - ketonylation

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8

Probe experiments using standard co-oxidants including copper(II) salts, benzoquinone, and PhI(OAc)₂ have not been productive.