Tris(trimethylsilyl)silane as a radical-based reducing agent in synthesis

Ballestri, Marco; Chatgilialoglu, Chryssostomos; Clark, K. B.; Griller, D.; Giese, Bernd; Kopping, B.

doi:10.1021/jo00002a035

Cited by 250 publications

(118 citation statements)

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“…The wide range of functional groups that can react with (Me 3 Si) 3 SiH includes isocyanides, reduced to the corresponding hydrocarbons. [18] Synthesis of secondary amines…”

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confidence: 99%

(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

Chatgilialoglu

2008

Chemistry A European J

150

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This Concept shows the flexibility and applicability of (Me3Si)3SiH in several synthetic transformations, such as radical reductions, consecutive radical reactions and hydrosilylation. The reactivity of (Me3Si)3SiH combines the multidisciplinary aspects of physical organic chemistry and organic synthesis, extending to polymers and materials science, as in the functionalization of flat silicon surfaces.

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“…The wide range of functional groups that can react with (Me 3 Si) 3 SiH includes isocyanides, reduced to the corresponding hydrocarbons. [18] Synthesis of secondary amines…”

mentioning

confidence: 99%

(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

Chatgilialoglu

2008

Chemistry A European J

150

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“…[16,17] Although the conversion of the dichloro derivative 13 into the monochloro form by the use of tributyltin hydride was previously reported (23 % yield), [17] we investigated the possibility to partially reduce the dichloro function by an alternative reducing agent. In our hands, tris(trimethylsilyl)silane, reported to be an efficient substitute for tributyltin hydride in radical-based reductions, [22] was able to convert 13 into 19 in good yield (63 %). Partial hydrolysis of 19 provided the monoester (AE )-20 (62 %) which was converted into the corresponding alcohol (AE )-21 by sodium borohydride reduction of the corresponding oxyanhydride (45 %).…”

Section: Resultsmentioning

confidence: 83%

Synthesis and Preliminary Biological Evaluation of 2′‐Substituted 2‐(3′‐Carboxybicyclo[1.1.1]pentyl)glycine Derivatives as Group I Selective Metabotropic Glutamate Receptor Ligands

et al. 2006

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The first series of 2'-substituted 2-(3'-carboxybicyclo[1.1.1]pentyl)glycine derivatives, (2R)- and (2S)-(2',2'-dichloro-3'-carboxybicyclo[1.1.1]pentyl)glycine (10) and (11), and 2-(2'-chloro-3'-carboxybicyclo[1.1.1]pentyl)glycine (12) were synthesized and evaluated as mGluR ligands. Compounds 11 and 12 were shown to be competitive group I mGluR antagonists. These results are also discussed in light of docking studies with both the active (closed) and inactive (open) conformations of mGluR1.

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“…On the other hand, the Saegusa oxidation procedure [9] with one equivalent of ferric chloride and pyridine (Entry 5) gave a diastereomeric mixture (77:23) of the chlorides 7a and 7b (trans-7a as the major isomer) even when ten equivalents of triethylsilane were used. However, treatment of these chlorides 7a and 7b with tris(trimethylsilyl)silane [10] afforded the expected oxacyclooctanone 8 (Entry 6).…”

Section: On the Synthesis Of Heliannuol Kmentioning

confidence: 99%

Strategies for the Total Asymmetric Synthesis of Heliannuols K and L: Scope and Limitations

2005

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Kulinkovich reactions of oxa‐esters bearing terminal double bonds afford cyclopropanols by intramolecular cyclization. These can undergo Saegusa oxidation to provide β‐chloro‐oxacycloalkanones and can then be then dehydrohalogenated into oxacycloalkenones. Through a judicious choice of starting esters, diverse aryl‐fused benzoxocinones possessing the basic skeleton of sesquiterpenes, such as heliannuols, can be obtained. Although the syntheses of certain compounds in racemic form seem accessible, however, improvements through new strategies are still required for the total asymmetric synthesis. This article describes the first synthesis of enantiomerically enriched OMe‐heliannuol K and the first stereo‐ and enantioselective synthesis of heliannuol L, and new approaches and studies of their limitations in the preparation of these products are detailed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Tris(trimethylsilyl)silane as a radical-based reducing agent in synthesis

Cited by 250 publications

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(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

Synthesis and Preliminary Biological Evaluation of 2′‐Substituted 2‐(3′‐Carboxybicyclo[1.1.1]pentyl)glycine Derivatives as Group I Selective Metabotropic Glutamate Receptor Ligands

Strategies for the Total Asymmetric Synthesis of Heliannuols K and L: Scope and Limitations

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Tris(trimethylsilyl)silane as a radical-based reducing agent in synthesis

Cited by 250 publications

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(Me3Si)3SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

(Me3Si)3SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

Synthesis and Preliminary Biological Evaluation of 2′‐Substituted 2‐(3′‐Carboxybicyclo[1.1.1]pentyl)glycine Derivatives as Group I Selective Metabotropic Glutamate Receptor Ligands

Strategies for the Total Asymmetric Synthesis of Heliannuols K and L: Scope and Limitations

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(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent

(Me₃Si)₃SiH: Twenty Years After Its Discovery as a Radical‐Based Reducing Agent