829-53-8Relevant academic research and scientific papers
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
supporting information, p. 4078 - 4084 (2019/10/28)
The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination
Bertrand, Xavier,Paquin, Jean-Fran?ois
supporting information, p. 9759 - 9762 (2019/11/28)
The use of a methanesulfonic acid/triethylamine trihydrofluoride combination for the direct hydrofluorination of methallyl-containing substrates is reported. Under those metal-free conditions that use readily available, cheap, and easy to handle reagents,
Catalytic, nucleophilic allylation of aldehydes with 2-substituted allylic acetates: Carbon-carbon bond formation driven by the water-gas shift reaction
Denmark, Scott E.,Matesich, Zachery D.
, p. 5970 - 5986 (2014/07/21)
The ruthenium-catalyzed allylation of aldehydes with allylic acetates has been expanded to incorporate substituents at the 2-position of the allylic components. Allylic acetates bearing a variety of substituents (CO 2-t-Bu, COMe, Ph, CH(OEt)su
Palladium-catalyzed divergent reactions of α-diazocarbonyl compounds with allylic esters: Construction of quaternary carbon centers
Chen, Zi-Sheng,Duan, Xin-Hua,Zhou, Ping-Xin,Ali, Shaukat,Luo, Jian-Yi,Liang, Yong-Min
supporting information; experimental part, p. 1370 - 1374 (2012/03/27)
Take two: α-Diazocarbonyl compounds display a diverse pattern of reactivity upon palladium-catalyzed reaction with esters. Esters bearing an alkynyl group on the carbonyl carbon atom lead to two different C-C bonds at the same carbon atom in a single operation through decarboxylation and migratory insertion, whereas aromatic and benzylic acid derivatives afford aromatic and benzylic esters bearing an O-substituted quaternary carbon center. Copyright
[Pd(μ-Br)(PtBu3)]2 as a highly active isomerization catalyst: Synthesis of enol esters from allylic esters
Mamone, Patrizia,Gruenberg, Matthias F.,Fromm, Andreas,Khan, Bilal A.,Goossen, Lukas J.
, p. 3716 - 3719 (2012/09/08)
The dimeric Pd(I)-complex [Pd(μ-Br)(PtBu3)] 2 was found to be highly active for catalyzing double-bond migration in various substrates such as unsaturated ethers, alcohols, amides, and arenes, under mild conditions. It efficiently mediates the conversion of allylic esters into enol esters, rather than inserting into the allylic C-O bond. The broad applicability of this reaction was demonstrated with the synthesis of 22 functionalized enol esters.
Tandem hydroformylation/Fischer indole synthesis: A novel and convenient approach to indoles from olefins
Koehling, Petra,Schmidt, Axel M.,Eilbracht, Peter
, p. 3213 - 3216 (2007/10/03)
(Matrix presented) A novel one-pot synthesis of indole systems via tandem hydroformylation/Fischer indole synthesis starting from olefins and arylhydrazines is described. This tandem procedure leads directly to 3-substituted indoles if unsubstituted phenylhydrazine is used and to 3,5- respectively 3,7-disubstituted indoles if para- or ortho-substituted arylhydrazines are used.
Magnesium bromide catalysed acylation of alcohols
Pansare, Sunil V.,Malusare, Mahesh G.,Rai, Anand N.
, p. 2587 - 2592 (2007/10/03)
Magnesium bromide is an efficient catalyst for the acetylation and benzoylation of a variety of primary and secondary alcohols with the respective acid anhydrides at ambient temperature. Acetylation of tertiary alcohols requires subambient temperature to suppress competing dehydration. Coordinating solvents retard the acylation process.
Photocycloelimination of α,α-dichlorocyclobutanones
Ramnauth, Jailall,Lee-Ruff, Edward
, p. 1245 - 1248 (2007/10/03)
Direct irradiation of a series of α,α-dichlorocyclobutanones in benzene solutions results in photocycloelimination to give 1,1-dichloroalkenes in yields ranging from 30-65%. The α,α-dichlorocyclobutanones were formed in good yields from the [2+2] cycloaddition of the terminal olefins with dichloroketene. This two-step sequence formally represents a "metathesis" of two olefinic functions and provides an easy access to functionalized 1,1-dichloroalkenes. Irradiation of the dichlorocyclobutanones in the solid state led to poor yields of 1,1-dichloroalkenes and polymeric mixtures, however, photoreactions performed in zeolites gave similar yields as those run in benzene solutions.
New methods for the synthesis of oxy-functionalizefd 1,2,4-trioxanes and 1,2,4-trioxepanes from unsaturated hydroperoxy acetals
Ushigoe, Yoshihiro,Masuyama, Araki,Nojima, Masatomo,McCullough, Kevin J.
, p. 8753 - 8756 (2007/10/03)
Oxy-functionalized 1,2,4-trioxanes or 1,2,4-trioxepanes were produced by either autoxidation of the unsaturated hydroperoxy acetals 1, or the acid-catalyzed cyclization of epox hydroperoxides 9 which were readily prepared from 1. By the appropriate choice of cyclization procedure, the structures of the resulting cyclic peroxides could be efficiently controlled.
