Recent Developments in the Synthesis and Structure of Organosilanols

At the Edge of Stability – Preparation of Methyl‐substituted Arylsilanetriols and Investigation of their Condensation Behavior

“…Consequently, we considered alkoxysilane 5c as a suitable precursor for the formation of 3c, since alkoxysilanes are favorable starting materials even for sensitive silanols under mild conditions. [18,42] Therefore, we subjected the literature known MesSi(OMe) 3 (5c) [43,44] to hydrolytic conditions with aqueous 0.5 vol-% acetic acid as reported by Korkin et al for the preparation of PhSi(OH) 3 . [41] In contrast to literature reports in related cases, no silanetriol formation could be observed by us after several hours or even one day.…”

Organotin compounds containing four‐membered distannoxane [Sn(µ‐OH)]2 units

“…26 A similar type of framework containing organostannoxane can be isolated from the reaction of [n-Bu 2 SnO] n with perchloric acid (Table 1, entry 19). 27 In the latter, the perchlorate anion is bound to tin by an η 1 28 -31 In all of these cases the carboxylate group binds to tin in a monodentate fashion. In an unusual example, the reaction of (Ph 3 Sn) 2 O with R f CO 2 H leads to an Sn-C bond cleavage and the isolation of [Ph 2 Sn(µ-OH)O 2 CR f ] 2 (Table 1, entry 24).…”

“…1), and can be prepared by utilizing a large number of preparative methods. 1 Such compounds are also of interest because of their utility as precursors for the preparation of metallosiloxanes. 1,3 -5 In contrast to the situation in silicon, organotin compounds containing the -OH group are not common.…”

Silanediol Hydrogen Bonding Activation of Carbonyl Compounds

“…While condensation is advantageous for the synthesis of siloxane polymers, metallosiloxanes, and silesquioxanes, [3] it creates a barrier that may hinder researchers from exploring the properties and applications of discrete silanediols. [4] Recent studies demonstrate that silanols can function as isosteres and transition-state analogues in drug design, in which the enhanced acidity of the silanol can improve binding to a receptor.[5] Small molecules containing silanol and silanediol groups may be useful as models to understand local surface sites and reactivity of silica materials for catalysis, and also to design new homogeneous small-molecule catalysts.We seek to understand the hydrogen bonding patterns and interactions between organic silanediols with carbonyls for applications to catalysis and molecular recognition. Hydrogen bonding interactions play an important role in molecular recognition and metal-free catalysis, and are frequently used in nature for structural organization and enzyme activity.…”