通过催化-h n偶联直接胺化唑类daiki mc成键data ole.pdfVIP

ORGANIC

LETTERS

DirectAminationofAzolesviaCatalytic2009

Vol.11,No.7

C-H,N-HCoupling1607-1610

DaikiMonguchi,TaikiFujiwara,HirotoshiFurukawa,andAtsunoriMori*

DepartmentofChemicalScienceandEngineering,KobeUniVersity,1-1Rokkodai,

Nada,Kobe657-8501,Japan

amori@kobe-u.ac.jp

ReceivedFebruary11,2009

C-H,N-HCouplingofazolestakesplacewithseveralaminesinthepresenceofacoppercatalysttoundergoaminationatthe2-position.

ThereactionofbenzothiazolewithN-methylanilineinthepresenceofsodiumacetateand20mol%Cu(OAc)2inxyleneunderanoxygen

atmosphereaffordedtheaminatedproductin81%yield.

Transition-metal-catalyzedC-Hfunctionalizationreactions(Buchwald-Hartwigreactions)6andorganometalliccom-

areofgreatinterestinorganicsynthesisbecausethereactionpounds(oxidativecoupling)havebeendevelopedsofar.7

showsanadvantageinatomefficiencycomparedtorelatedIncontrast,limitedexamplesareshownforintra-and8

cross-couplingwithorganometalliccompounds.1Thereac-

(4)(a)Mori,A.;Sekiguchi,A.;Masui,K.;Shimada,T.;Horie,M.;

tionofheteroaromaticcompoundsisparticularlyimportantOsakada,K.;Kawamoto,M.;Ikeda,T.J.Am.Chem.Soc.2003,125,1700.

becauseoftheirwideutilitiesinthesynthesisofbiologically(b)Kobayashi,K.;Sugie,A.