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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>
Raja, Gabriel Charles Edwin,Ryu, Ji Yeon,Lee, Junseong,Lee, Sunwoo American Chemical Society 2017 Organic letters Vol.19 No.24
<P>Homoisoflavonoids were formed in DMSO exclusively, and flavones were formed in <I>t</I>-AmOH when salicylaldehyde and alkynoic acids reacted with [Ru(<I>p</I>-cymene)Cl<SUB>2</SUB>]<SUB>2</SUB> and CsOAc. They were formed through C–H activation of salicylaldehyde and decarboxylative coupling of alkynoic acid. This reaction system showed good yields, broad substrate scope, and good functional group tolerance. It was found that chalcone was an intermediate in the formation of both homoisoflavonoid and flavone.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2017/orlef7.2017.19.issue-24/acs.orglett.7b03325/production/images/medium/ol-2017-033254_0009.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol7b03325'>ACS Electronic Supporting Info</A></P>
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.
Park, Jaerim,Kim, Ji Dang,Raja, Gabriel Charles Edwin,Choi, Hyun Chul,Lee, Sunwoo Informa UK (TaylorFrancis) 2017 Synthetic communications Vol.47 No.21
<P>Cyclic anhydrides such as naphtho[2,3-c]furan-1,3-dione derivatives were synthesized from the reaction of arylpropiolic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of N-methylmorpholine at room temperature. This mild condition provided the naphtho[2,3-c]furan-1,3-dione derivatives in good yields. Spectroscopic analysis suggested that the formation of arylpropiolate is the rate-determining step.</P>