Rapid, Regioconvergent, Solvent-Free Alkene Hydrosilylation with a Cobalt Catalyst

Chen, Chi; Hecht, Maxwell B.; Kavara, Aydin; Brennessel, William W.; Mercado, Brandon Q.; Weix, Daniel J.; Holland, Patrick L.

doi:10.1021/jacs.5b08611

Cited by 200 publications

(94 citation statements)

References 38 publications

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“…Chen et al reported a cobalt-based catalyst for the anti-Markovnikov alkene hydrosilylation under solvent-free conditions at low temperatures and low catalyst loadings ( Figure 39) [116]. Additionally, the catalysts can be synthesized in-situ from commercially available, low-cost precursors under ambient conditions giving high yields/selectivity for functionalized alkenes (namely 1a = 89%/>98%, 1b = 94%/98%, 1c = 89%/98%).…”

Section: High Efficient/low-cost Hydrosilylation (Solvent-free Conditmentioning

confidence: 99%

Fifty Years of Hydrosilylation in Polymer Science: A Review of Current Trends of Low-Cost Transition-Metal and Metal-Free Catalysts, Non-Thermally Triggered Hydrosilylation Reactions, and Industrial Applications

2017

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Hydrosilylation reactions, the (commonly) anti-Markovnikov additions of silanes to unsaturated bonds present in compounds such as alkenes and alkynes, offer numerous unique and advantageous properties for the preparation of polymeric materials, such as high yields and stereoselectivity. These reactions require to be catalyzed, for which platinum compounds were used in the initial stages. Celebrating the 50th anniversary of hydrosilylations in polymer science and, concomitantly, five decades of continuously growing research, hydrosilylation reactions have advanced to a level that renders them predestined for transfer into commercial products on the large scale. Facing this potential transfer, this review addresses and discusses selected current trends of the scientific research in the area, namely low-cost transition metal catalysts (focusing on iron, cobalt, and nickel complexes), metal-free catalysts, non-thermally triggered hydrosilylation reactions (highlighting stimuli such as (UV-)light), and (potential) industrial applications (highlighting the catalysts used and products manufactured). This review focuses on the hydrosilylation reactions involving alkene reactants.

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Section: High Efficient/low-cost Hydrosilylation (Solvent-free Conditmentioning

confidence: 99%

Fifty Years of Hydrosilylation in Polymer Science: A Review of Current Trends of Low-Cost Transition-Metal and Metal-Free Catalysts, Non-Thermally Triggered Hydrosilylation Reactions, and Industrial Applications

2017

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“…Speier and Karstedt have demonstrated the use of platinum catalysts for direct Si‐H bond activation in hydrosilylation, and has been employed in industrial‐scale manufacturing . Intensive research in hydrosilylation have led to the discovery of other effective catalysts such as earth‐abundant Fe, Ni, and Co metals . In addition, recent advancement demonstrated the metal‐free hydrosilylation using electron‐deficient borane Lewis acid catalysts …”

Section: Hydrosilylation Via Photo‐generated Silyl Radicalsmentioning

confidence: 99%

Recent Developments in the Photo‐Mediated Generation of Silyl Radicals and Their Application in Organic Synthesis

2018

ChemPhotoChem

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“…The scope for the unsaturated substrate is versatile, including alkene,, , alkyne, carbonyl, and carboxylic derivative groups. Additionally, a number of different silanes can be used: much research is performed with phenylsilane, and other silanes such as diphenylsilane, alkyl silanes, and alkoxy silanes, can be employed as well.…”

Section: Introductionmentioning

confidence: 99%

Cobalt(II) and (I) Complexes of Diphosphine‐Ketone Ligands: Catalytic Activity in Hydrosilylation Reactions

et al. 2019

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The hydrosilylation of unsaturated compounds homogeneously catalyzed by cobalt complexes has gained considerable attention in the last years, aiming at substituting precious metal‐based catalysts. In this study, the catalytic activity of well‐characterized CoII and CoI complexes of the pToldpbp ligand is demonstrated in the hydrosilylation of 1‐octene with phenylsilane. The CoI complex is the better precatalyst for the mentioned reaction under mild conditions, at 1 mol‐% catalyst, 1 h, room temperature, and without solvent, yielding 84 % of octylphenylsilane. Investigation of the substrate scope shows lower performance of the catalyst in styrene hydrosilylation, but excellent results with allylbenzene (84 %) and acetophenone (> 99 %). This catalytic study contributes to the field of cobalt‐catalyzed hydrosilylation reactions and shows the first example of catalysis employing the dpbp ligand in combination with a base metal.

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Rapid, Regioconvergent, Solvent-Free Alkene Hydrosilylation with a Cobalt Catalyst

Cited by 200 publications

References 38 publications

Fifty Years of Hydrosilylation in Polymer Science: A Review of Current Trends of Low-Cost Transition-Metal and Metal-Free Catalysts, Non-Thermally Triggered Hydrosilylation Reactions, and Industrial Applications

Fifty Years of Hydrosilylation in Polymer Science: A Review of Current Trends of Low-Cost Transition-Metal and Metal-Free Catalysts, Non-Thermally Triggered Hydrosilylation Reactions, and Industrial Applications

Recent Developments in the Photo‐Mediated Generation of Silyl Radicals and Their Application in Organic Synthesis

Cobalt(II) and (I) Complexes of Diphosphine‐Ketone Ligands: Catalytic Activity in Hydrosilylation Reactions

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