Hydrosilane σ‐Adduct Intermediates in an Adaptive Zinc‐Catalyzed Cross‐dehydrocoupling of Si−H and O−H Bonds

Patnaik, Smita; Kanbur, Uddhav; Ellern, Arkady; Sadow, Aaron D.

doi:10.1002/chem.202101146

Title: Hydrosilane σ‐Adduct Intermediates in an Adaptive Zinc‐Catalyzed Cross‐dehydrocoupling of Si−H and O−H Bonds

Journal Article · 20 May 2021 · Chemistry - A European Journal

DOI: https://doi.org/10.1002/chem.202101146 · OSTI ID:1784396

Patnaik, Smita ^[1]; Kanbur, Uddhav ^[1]; Ellern, Arkady ^[2];

^[1]

Department of Chemistry Iowa State University Ames IA 50011 USA, US Department of Energy Ames Laboratory Iowa State University Ames IA 50011 USA
Department of Chemistry Iowa State University Ames IA 50011 USA

Abstract Three‐coordinate ^Ph BOX ZnR ( ^Ph BOX =phenyl‐(4,4‐dimethyl‐oxazolinato; R=Me: 2 a , Et: 2 b ) catalyzes the dehydrocoupling of primary or secondary silanes and alcohols to give silyl ethers and hydrogen, with high turnover numbers (TON; up to 10 ⁷ ) under solvent‐free conditions. Primary and secondary silanes react with small, medium, and large alcohols to give various degrees of substitution, from mono‐ to tri‐alkoxylation, whereas tri‐substituted silanes do not react with MeOH under these conditions. The effect of coordinative unsaturation on the behavior of the Zn catalyst is revealed through a dramatic variation of both rate law and experimental rate constants, which depend on the concentrations of both the alcohol and hydrosilane reactants. That is, the catalyst adapts its mechanism to access the most facile and efficient conversion. In particular, either alcohol or hydrosilane binds to the open coordination site on the ^Ph BOX ZnOR catalyst to form a ^Ph BOX ZnOR(HOR) complex under one set of conditions or an unprecedented σ‐adduct ^Ph BOX ZnOR(H−SiR′ ₃ ) under other conditions. Saturation kinetics provide evidence for the latter species, in support of the hypothesis that σ‐bond metathesis reactions involving four‐centered electrocyclic 2σ–2σ transition states are preceded by σ‐adducts.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1784396

Report Number(s):: IS-J-10,491

Journal Information:: Chemistry - A European Journal, Journal Name: Chemistry - A European Journal Journal Issue: 40 Vol. 27; ISSN 0947-6539

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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