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Copper-catalyzed Decarboxylative Hydroboration: Synthesis of Vinyl Boronic Esters
Francis Mariaraj Irudayanathan,Gabriel Charles Edwin Raja,김한성,나경수,이선우 대한화학회 2016 Bulletin of the Korean Chemical Society Vol.37 No.4
Vinyl boronic esters were synthesized from aryl alkynyl carboxylic acids and bis(pinacolato)diboron using a copper-catalyzed decarboxylative reaction. The reaction was conducted with CuI (10 mol%), bis-[2-(diphenylphosphino)phenyl]ether(20 mol%), and LiOMe (20 mol%) in DMSO at 50 °C for 16 h. This method provided the desired vinyl boronic esters in good-to-moderate yields and showed good functional group tolerance.
Irudayanathan, Francis Mariaraj,Lee, Sunwoo THE AMERICAN CHEMICAL SOCIETY 2017 ORGANIC LETTERS Vol.19 No.9
<P>Allyl nitriles were synthesized from the reactions of arylpropiolic acids with azobis(alkylcarbonitriles) (AIBN or ACCN). In the presence of Cu(OAc)(2) as a catalyst and pyridine as the solvent, the (E)-stereoisomer was formed as the major product. This transformation shows good tolerance toward alkoxy, halogen, alcohol, amine, ester, and ketone functional groups. When the reaction was conducted with the sterically bulky amine, ethyldiisopropylamine, in the absence of a copper catalyst, the corresponding (Z)-stereoisomers were formed preferentially.</P>
Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes
Edwin Raja, Gabriel Charles,Irudayanathan, Francis Mariaraj,Kim, Han-Sung,Kim, Jimin,Lee, Sunwoo American Chemical Society 2016 Journal of organic chemistry Vol.81 No.12
<P>A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni(acac)<SUB>2</SUB> and 1,10-phenanthroline showed the best result in the presence of CsF and CuF<SUB>2</SUB> at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2016/joceah.2016.81.issue-12/acs.joc.6b00883/production/images/medium/jo-2016-00883y_0009.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo6b00883'>ACS Electronic Supporting Info</A></P>