Silatrane as a Practical and Selective Reagent for the Reduction of Aryl Aldehydes to Benzylic Alcohols

Abstract

Hydrosilanes are cheap, readily available substrates, yet they do not see as extensive use for simple carbonyl reductions as borohydrides. Hydrosilane reducing agents broadly fall into one of two general categories: either a) they are easy to handle and require expensive and/or hazardous additives, or b) they are difficult and/or dangerous to handle. This work details the discovery of mild and functional group compatible condi-

1‐Hydrosilatrane: A Locomotive for Efficient Ketone Reductions

“…This work was narrow in scope and, furthermore, irreproducible in our hands. However, we were inspired and proceeded to develop a method for the reduction of aldehydes by using 1 in the presence of a Lewis base activator . Herein, we discuss the activation of 1‐hydrosilatrane ( 1 ) with a Lewis base to reduce ketones in an operationally simple manner, as well as the scope and stereoselectivity of the reaction.…”

One-Pot Reductive Acetylation of Aldehydes using 1-Hydrosilatrane in Acetic Acid

“…Recently, our group has developed several reductive methods using 1-hydrosilatrane ( Figure 1). Our research program has led to the development of a direct route for the reduction of aldehydes and ketones to their corresponding alcohols 20,21 and direct reductive aminations of aldehydes and ketones in the presence of an amine. 22 1-Hydrosilatrane is an attractive reducing agent because it is air-and moisture-stable, inexpensive, and simple to synthesize.…”

Hydrosilylation and hydroboration in a sustainable manner: from Earth-abundant catalysts to catalyst-free solutions

“…3). 75,76 This is a very interesting alternative to simple hydrosilanes. 1-Hydrosilatrane is very expensive in the commercial market, but it might be individually synthesized from cheap and easily accessible reagents, and finally, it can be stored for several months without any special handling.…”