150614-90-7Relevant academic research and scientific papers
Cu-Catalyzed Carbonylative Silylation of Alkyl Halides: Efficient Access to Acylsilanes
Cheng, Li-Jie,Mankad, Neal P.
supporting information, p. 80 - 84 (2020/01/09)
A Cu-catalyzed carbonylative silylation of unactivated alkyl halides has been developed, enabling efficient synthesis of alkyl-substituted acylsilanes in high yield. A variety of functional groups are tolerated under the mild reaction conditions, and prim
Zinc-Catalyzed Synthesis of Acylsilanes Using Carboxylic Acids and a Silylborane in the Presence of Pivalic Anhydride
Tatsumi, Kenta,Tanabe, Sae,Tsuji, Yasushi,Fujihara, Tetsuaki
supporting information, p. 10130 - 10133 (2019/12/24)
Zinc-catalyzed synthesis of acylsilanes using carboxylic acids and a silylborane has been achieved in the presence of pivalic anhydride. Various carboxylic acids were converted to the corresponding acylsilanes. The in situ formation of mixed anhydrides wa
Tertiary α-Silyl Alcohols by Diastereoselective Coupling of 1,3-Dienes and Acylsilanes Initiated by Enantioselective Copper-Catalyzed Borylation
Feng, Jian-Jun,Oestreich, Martin
supporting information, p. 8211 - 8215 (2019/05/27)
An efficient synthesis of functionalized tertiary α-silyl alcohols by an enantio- and diastereoselective copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3-dienes and a broad range of aryl- as well as alkenyl- but also alkyl-substituted acylsilanes. The target compounds are formed with high regio-, diastereo-, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks.
Synthesis of acylsilanes by copper(I)-catalyzed addition of silicon nucleophiles onto acid derivatives
Cirriez, Virginie,Rasson, Corentin,Riant, Olivier
supporting information, p. 3137 - 3140 (2013/12/04)
The transition metal-catalyzed transfer of silicon nucleophiles onto various electrophiles has recently gained considerable attention, due to the now readily available silicon pro-nucleophiles such as silylboronates. Our interest lies in the addition of such species to acid derivatives for the generation of acylsilanes. We report herein an efficient method to synthesize these compounds, starting from easy-to-form anhydrides, with very good yields. Copyright
Synthesis of acylsilanes by palladium-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides
Azuma, Hiroki,Okano, Kentaro,Tokuyama, Hidetoshi
, p. 959 - 961 (2011/12/05)
An acylsilane synthesis by a Pd-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides was developed. S-Phenyl thiol esters with a variety of functional groups were converted to corresponding acylsilanes.
Efficient synthesis of acylsilanes using morpholine amides
Clark, Christopher T.,Milgram, Benjamin C.,Scheidt, Karl A.
, p. 3977 - 3980 (2007/10/03)
(Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.
Synthesis of functionalized acylsilanes from carboxylic acid chlorides and silyl-zinc cyanocuprates
Bonini,Comes-Franchini,Mazzanti,Passamonti,Ricci,Zani
, p. 92 - 96 (2007/10/02)
The high yielding synthesis of a variety of acylsilanes, most of them unknown and bearing reactive functionalities, has been accomplished by reaction between carboxylic acid chlorides and a novel silyl-zinc cyanocuprate acting as a silyl anion source. The advantages offered by this procedure with respect to those previously reported, based on carboxylic acid chlorides or on different starting materials, as well as with respect to the use of standard silyl cyanocuprates, are discussed herein.
Synthesis of Acylsilanes from Amides and Esters, and the Selective Oxidation of α-Silyl Alcohols to Aldehydes
Fleming, Ian,Ghosh, Usha
, p. 257 - 262 (2007/10/02)
The acylsilanes 2 can easily be made directly from the dimethylamides 3 by treatment with phenyldimethylsilyllithium.They can also be made in two steps from the esters 4 using 2 equiv. of phenyldimethylsilyllithium followed by oxidation of the disilyl alcohols 5 with PDC.The disilyl alcohols 5 can be used as intermediates in the conversion of esters into aldehydes without recourse to hydride reagents, by monodesilylation, using a Brook rearrangement, followed by oxidation and selective removal of the silyl group, using chromium trioxide in DMSO.
Chemistry of Silyl Thioketones. Part 7. Synthesis, Cycloaddition and Oxidation of Cycloalkyl Silyl Thioketones and Desilylation of the Reaction Products
Bonini, Bianca F.,Busi, Filippo,Laet, Roland C. de,Mazzanti, Germana,Thuring, Jan-Willem J. F.,et al.
, p. 1011 - 1018 (2007/10/02)
Cycloalkyl silyl thioketones 3, achiral as well as chiral at carbon, have been synthesized by thionation of the corresponding acyl silanes 2.During thionation of 2a, 2d and 2f unexpected products were observed.Cycloaddition reactions of cycloalkyl silyl thioketones 3 with buta-1,3-diene have been performed.A diastereoisomeric excess (d.e.) of 80percent was obtained in the case of chiral thione 3e.Desilylation of the cycloadducts was only possible at the stage of the corresponding α-silyl sulfones 11.Oxidation of compounds 3 led to the corresponding (E)-silyl sulfines 13 which by stereospecific fluorodesilylation gave (Z)-thioaldehyde S-oxides 14.Compound 14e is the first example of enantiomerically pure mono-substituted sulfine (thioaldehyde S-oxide).
