16031-55-3Relevant academic research and scientific papers
Cobalt-Catalyzed Intermolecular Hydrofunctionalization of Alkenes: Evidence for a Bimetallic Pathway
Zhou, Xiao-Le,Yang, Fan,Sun, Han-Li,Yin, Yun-Nian,Ye, Wei-Ting,Zhu, Rong
supporting information, p. 7250 - 7255 (2019/05/16)
A functional group tolerant cobalt-catalyzed method for the intermolecular hydrofunctionalization of alkenes with oxygen- and nitrogen-based nucleophiles is reported. This protocol features a strategic use of hypervalent iodine(III) reagents that enables a mechanistic shift from conventional cobalt-hydride catalysis. Key evidence was found supporting a unique bimetallic-mediated rate-limiting step involving two distinct cobalt(III) species, from which a new carbon-heteroatom bond is formed.
Iron-Catalyzed Acyloxyalkylation of Styrenes Using Hypervalent Iodine Reagents
Wang, Zijia,Kanai, Motomu,Kuninobu, Yoichiro
supporting information, p. 2398 - 2401 (2017/05/12)
Iron-catalyzed acyloxyalkylation of styrene derivatives using hypervalent iodine reagents was achieved. The acyloxyalkylation reaction proceeded using various types of styrenes and hypervalent iodine reagents. The acyloxyalkylated products were obtained in moderate to good yields without loss of the functional groups. The reaction proceeded via the formation of radical species derived from hypervalent iodine reagents by decarboxylation.
A novel synthesis of isoeugenol, [ring-(U)-14C]
Immoos, John E.
, p. 419 - 424 (2015/11/18)
A novel method for the preparation of isoeugenol, [ring-(U)-14C] is presented. Phenols and phenyl esters substituted in the para position with 1-hydroxyethyl or 1-hydroxypropyl acetate esters when treated with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide (DMF) eliminate the alkyl carboxylate function to give the unsaturated compound. The reaction fails with unsubstituted or ether substituted phenyl 1-hydroxyacetate esters.
Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation
Wang, Yin,Zhang, Lei,Yang, Yunhui,Zhang, Ping,Du, Zhenting,Wang, Congyang
supporting information, p. 18048 - 18051 (2014/01/06)
Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.
Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides
Powell, David A.,Pelletier, Guillaume
, p. 2495 - 2498 (2008/09/19)
A copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates has been developed which is suitable for the coupling of a wide variety of functionalized sulfonamide nucleophiles with acetate electrophiles. The methodology allows for the amidation of benzylic substrates which are not further activated by an additional adjacent alkene or alkyne, enabling simple allylic acetates and primary benzylic acetates to be used as reaction partners.
DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation
Kumar, Vinod,Sharma, Abhishek,Sharma, Meenakshi,Sharma, Upendra K.,Sinha, Arun K.
, p. 9718 - 9723 (2008/02/12)
Acetoxylated arylalkanes are selectively obtained via sonochemical activation of DDQ catalyzed benzylic oxidation of arylalkanes in the presence of anhydrous acetic acid. The method gives an exquisite control of benzylic acetoxylation under ultrasound, in contrast to the uncontrolled oxidation observed under conventional heating or microwave activation. In addition, the developed method could be?a useful strategy for the synthesis of industrially important enantiopure benzyl alcohols due to the easy amenability of obtained acetoxylated products toward chiral resolution.
The chemistry of acylals. Part I. The reactivity of acylals towards Grignard and organolithium reagents
Sydnes, Leiv K.,Sandberg, Marcel
, p. 12679 - 12690 (2007/10/03)
Aldehyde acylals have been prepared and reacted with Grignard and alkyllithium reagents. Acylals from formaldehyde furnished complex reaction mixtures when reacted with both reagents. Acylals of other aldehydes gave reaction mixtures that consisted mainly of an ester, generated by replacing one of the carboxy groups with the organic part of the organometallic reagent, and regenerated aldehyde. The esters were formed in the highest yields. Yields above 90% were experienced when the acylals were reacted with Grignard reagents under Barbier conditions.
