5908-41-8Relevant articles and documents
Anodic oxidation of 2-alkyl-2-trialkylsilyl-1, 3-dithianes a facile preparation of acylsilanes
Suda, Kohji,Watanabe, Jun-Ichi,Takanami, Toshikatsu
, p. 1355 - 1356 (1992)
Acylsilanes can easily be prepared by the anodic oxidation of 2-alkyl-2-trialkylsilyl-1, 3-dithianes with a platinum anode in wet acetonitrile. This electrochemical reaction provides a general and convenient access to aroyl, saturated and α, β-unsaturated
Synthesis of aryl and alkyl acylsilanes using trimethyl(tributylstannyl)silane
Geng, Feng,Maleczka Jr., Robert E.
, p. 3113 - 3114 (1999)
Palladium catalyzed coupling of acid chlorides and trimethyl(tribuhfistannyl)silane proves to be a convenient method for the preparation of both aromatic and aliphatic acylsilanes.
Visible-Light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes
Reimler, Jannik,Studer, Armido
supporting information, p. 15392 - 15395 (2021/10/04)
A method for the selective tryptophan modification and labelling of tryptophan-containing peptides is described. Photoirradiation of acylsilanes generates reactive siloxycarbenes which undergo H?N-insertion into the indole moiety of tryptophan to give stable silyl protected hemiaminals. This method is successfully applied to chemically modify various tryptophan containing oligopeptides. The method enables the selective introduction of alkynes to peptides that are eligible for further alkyne-azide click chemistry. In addition, the dansyl fluorophore can be conjugated to a peptide using this approach.
Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions
Deng, Xingwang,Zhou, Guan,Tian, Jing,Srinivasan, Rajavel
supporting information, p. 7024 - 7029 (2020/12/29)
We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.
Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide
Fan, Zhengning,Yi, Yaping,Chen, Shenhao,Xi, Chanjuan
supporting information, p. 2303 - 2307 (2021/04/05)
Intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide (CO2) was achieved by photoirradiation under catalyst-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of the acylsilanes added to the C═O bond of CO2 to give α-ketocarboxylates, which underwent hydrolysis to afford α-ketocarboxylic derivatives in good yields. Control experiments suggest that the generated siloxycarbene is likely to be from the singlet state (S1) of the acylsilane and the addition to CO2 is not in a concerted manner.
Ruthenium-Catalyzed Brook Rearrangement Involved Domino Sequence Enabled by Acylsilane-Aldehyde Corporation
Lu, Xiunan,Zhang, Jian,Xu, Liangyao,Shen, Wenzhou,Yu, Feifei,Ding, Liyuan,Zhong, Guofu
supporting information, p. 5610 - 5616 (2020/07/24)
A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino sequence is presented to prepare highly functionalized silyloxy indenes with atomic- and step-economy. This domino reaction is triggered by acylsilane-directed C-H activation, and the aldehyde controlled the subsequent enol cyclization/Brook Rearrangement other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyloxy indenes allows access to a diverse range of interesting indene and indanone derivatives.
Controllable one-pot synthesis for scaffold diversity: Via visible-light photoredox-catalyzed Giese reaction and further transformation
Nam, Su Been,Khatun, Nilufa,Kang, Young Woo,Park, Boyoung Y.,Woo, Sang Kook
, p. 2873 - 2876 (2020/03/19)
This study presents a controllable one-pot synthesis for constructing valuable scaffolds (alcohols, 2,3-dihydrofurans, α-cyano-γ-butyrolactones, and γ-butyrolactones) via a visible-light photoredox-catalyzed Giese reaction and further transformation. This
Preparation of Functionalized Acylsilanes by Diol Cleavage of Cyclic 1,2-Dihydroxysilanes
Zimdars, Patrick,B?hlig, Kristin,Metz, Peter
, p. 6163 - 6167 (2019/08/20)
We report a study on diol cleavage of cyclic 1,2-dihydroxysilanes for the preparation of functionalized acylsilanes. Sodium periodate turned out to be an efficient reagent for this transformation, resulting in good to excellent yields. The method is chara
Synthesis of Acylsilanes via Catalytic Dedithioacetalization of 2-Silylated 1,3-Dithianes with 30% Hydrogen Peroxide
Kirihara, Masayuki,Suzuki, Satoshi,Ishihara, Naohiro,Yamazaki, Kento,Akiyama, Tomomi,Ishizuka, Yuki
, p. 2009 - 2014 (2017/04/26)
Acylsilanes were obtained efficiently from dedithioacetalization of 2-silylated 1,3-dithianes using 30% hydrogen peroxide catalyzed by iron(III) acetylacetonate-sodium iodide. The use of niobium(V) chloride as a catalyst instead of iron(III) acetylacetonate was also effective, except in synthesizing some acyltrimethylsilanes.
Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations
Deng, Yifan,Liu, Qi,Smith, Amos B.
supporting information, p. 9487 - 9490 (2017/07/24)
Oxidative [1,2]-Brook rearrangements via hypervalent silicon intermediates induced by photoredox-catalyzed single-electron transfer have been achieved, permitting the formation of reactive radical species that can engage in alkylations and arylations.