68185-94-4Relevant academic research and scientific papers
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.
Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations
Deng, Yifan,Liu, Qi,Smith, Amos B.
, 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.
Palladium-catalyzed carbonylative coupling reactions of aryl iodides with hexamethyldisilane (HMDS) to benzoyl silanes
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
experimental part, p. 582 - 584 (2012/02/02)
A novel procedure for the palladium-catalyzed carbonylative synthesis of acyl silanes has been developed. Starting from aryl iodides and hexamethyldisilane (HMDS) various benzoyl silanes are produced in moderate to good yields.
One-pot preparation of aroylsilanes by reductive silylation of methyl benzoates
Tongco, Emily C.,Wang, Qunjie,Prakash, G.K. Surya
, p. 2117 - 2123 (2007/10/03)
A one-pot synthesis of aroylsilanes based on reductive silylation of methyl benzoates using Mg/I2/chlorosilane in nontoxic 1-methyl-2- pyrrolidinone (NMP) solvent, is described. The yields are moderate to good and the method has been used for the preparation of some new bifunctional aroylsilanes.
PREPARATION OF SUBSTITUTED BENZOYLTRIMETHYLSILANES BY THE PALLADIUM-CATALYZED SILYLATION OF SUBSTITUTED BENZOYL CHLORIDES WITH HEXAMETHYLDISILANE
Yamamoto, Keiji,Suzuki, Shigeaki,Tsuji, Jiro
, p. 1653 - 1656 (2007/10/02)
A direct preparative route to benzoyltrimethylsilane has been found by the reaction of benzoyl chloride with hexamethyldisilane in the presence of a specified palladium(II) complex as catalyst.
