Catalytic hydrosilylation of organic esters using manganese carbonyl acetyl complexes.

Mao, Zhibiao; Gregg, Brian T.; Cutler, Alan R.

doi:10.1021/ja00145a036

Cited by 132 publications

(90 citation statements)

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“…However, the generality of this reaction was not demonstrated, as only one ester was cleanly converted into the corresponding ether (Scheme 6). [19] More recently, Sakai et al reported a more general system for the reduction of esters to ethers. They used indium bromide as the catalyst and triethyl silane as the hydride source.…”

Section: Reduction Of Estersmentioning

confidence: 99%

Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation

et al. 2011

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In the last decade, an increasing number of useful catalytic reductions of carboxylic acid derivatives with hydrosilanes have been developed. Notably, the combination of an appropriate silane and catalyst enables unprecedented chemoselectivity that is not possible with traditional organometallic hydrides or hydrogenation catalysts. For example, amides and esters can be reduced preferentially in the presence of ketones or even aldehydes. We believe that catalytic hydrosilylations will be used more often in the future in challenging organic syntheses, as the reaction procedures are straightforward, and the reactivity of the silane can be fine-tuned. So far, the synthetic potential of these processes has clearly been underestimated. They even hold promise for industrial applications, as inexpensive and readily available silanes, such as polymethylhydrosiloxane, offer useful possibilities on a larger scale.

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Section: Reduction Of Estersmentioning

confidence: 99%

Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation

et al. 2011

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“…A problem remains in preparation of the catalyst which is preferentially available by photochemical activation then by thermal reaction. Nagashima and co-workers 79 have introduced in this reaction a new catalytic system consisting of a trirhuteniumcarbonyl cluster and aromatic ligands as bridges, structures 52 and 53 (Scheme 17).…”

Section: Scheme 16mentioning

confidence: 99%

“…In the same paper the authors have studied selectivity of 53 in reduction of some other esters and lactones to ethers. 79 It turned out that reduction of lactones to cyclic ethers proceeds with significantly higher selectivity then for acyclic ethers, and that the later can be reduced with higher selectivity in dioxane then in tetrahydropyrane.…”

Section: Scheme 16mentioning

confidence: 99%

Ethers from esters; from exceptional transformation to synthetic method

Jakopović¹,

Kapić²,

Alihodžić³

et al. 2015

Arkivoc

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Most ether-bond forming reactions based on traditional methods or modifications thereof require strongly acidic or basic conditions and often harsh reaction conditions. Reduction of esters to ethers has been regarded as an impracticable method, generally affording alcohols as the principal products. Only recently, original, mostly catalytic methods for reduction of esters to ethers have been reported, which proceed under mild conditions and are compatible with many functional groups present in the substrate ester molecule. These reactions are considered as a valuable alternative to traditional methods, and specific protocols have been reported. An account of the progress in this synthetic methodology is given.

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“…[12][13][14][15] Silicon chemistry combined with the use of organometallic complexes appears to be a good alternative. [16] Silanes and siloxanes have been employed with different metal sources such as Sb, [17] Rh, [18] Ru, [19] Mn, [20] Ti, [21,22] In, [23] Mo, [24] and Zn [25] to afford alcohols, ethers, or aldehydes. Fluoride salts were also used to prepare alcohols.…”

Section: Introductionmentioning

confidence: 99%