Pd/O_2体系中邻炔基苯乙烯类衍生物的氯钯化/Heck串联反应研究
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摘要
在Pd/O_2体系中,邻炔基苯乙烯类衍生物经过氯钯化/Heck偶联多步串联反应,获得了13个3位氯取代茚类化合物.该方法以氧气为唯一氧化剂,以氯化锂为氯源,避免了过量氯化铜的加入,具有绿色环保、条件温和、产率高和底物普适性较好等特点.
An economic and environmental synthestic method for 3-chloroindenes from o-(alkynyl)styrenes through tandem reactions including choropalladation/Heck cross coupling in Pd/O_2 system was reported. Taking green dioxygen as sole oxidant and LiCl as chlorine source, 13 functionalized 3-chloroindenes could be synthesized in moderate to high yield without the addition of CuCl_2
An economic and environmental synthestic method for 3-chloroindenes from o-(alkynyl)styrenes through tandem reactions including choropalladation/Heck cross coupling in Pd/O_2 system was reported. Taking green dioxygen as sole oxidant and LiCl as chlorine source, 13 functionalized 3-chloroindenes could be synthesized in moderate to high yield without the addition of CuCl_2
引文
[1]Selected review and examples on chloropalladation,please see:(a)Lu,X.In Handbook of Organopalladium Chemistry for Organic Synthesis,Ed.:Negishi,E.,Wiley-Interscience,New York,2002,Vol.2,pp.2267~2288.(b)Huang,L.;Wang Q.;Liu,X.;Jiang,H.Angew.Chem.,Int.Ed.2012,51,5696.(c)Huang,L.;Wang,Q.;Wu,W.;Jiang,H.J.Org.Chem.2014,79,7734.(d)Zhang,Z.;Ouyang,L.;Wu,W.;Li,J.;Zhang,Z.;Jiang,H.J.Org.Chem.2014,79,10734.(e)Sun,N.;Li,Y.;Yin,G.;Jiang,S.Eur.J.Org.Chem.2013,2541.(f)Zhang,Z.;Wu,W.;Liao,J.;Li,J.;Jiang,H.Chem.-Eur.J.2015,21,6708.(g)Derosa,J.;Cantu,A.L.;Boulous,M.N.;O'Duill,M.L.;Turnbull,J.L.;Liu,Z.;Torre,D.L.T.;Engle,K.M.J.Am.Chem.Soc.2017,139,5183.(h)Li,J.;Hu,W.;Li,C.Yang,S.;Wu,W.;Jiang,H.Org.Chem.Front.2017,4,373.
[2]Selected examples on chloropalladation with Cu Cl2:(a)Huang,J.;Dong,Y.;Wang,X.;Luo,H.Chem.Commun.2010,46,1035.(b)An,Y.;Li,J.;Zhang,Z.;Li,C.;Yang,S.Chin.J.Org.Chem.2016,36,2136(in Chinese).(安艳妮,李建晓,张振明,李春生,杨少容,有机化学,2016,36,2136.)(c)Li,J.;Li,C.;Yang,S.;Luo,W.Chin.J.Org.Chem.2015,35,898(in Chinese).(李建晓,李春生,杨少容,罗维,有机化学,2015,35,898.)
[3]Review on the reactions with O2:(a)Wu,W.;Jiang,H.Acc.Chem.Res.2012,45,1736.(b)Wu,W.;Jiang,H.Acc.Chem.Res.2014,47,2483.(c)Wu,K.;Song,C.;Cui,D.Chin.J.Org.Chem.2017,37,586(in Chinese).(吴空,宋婵,崔冬梅,有机化学,2017,37,586.)(d)Cheng,X.;Hu,X.;Lu,Z.Chin.J.Org.Chem.2017,37,251(in Chinese).(程骁恺,胡新根,陆展,有机化学,2017,37,251.)(e)Xu,J.;Song,Q.Chin.J.Org.Chem.2016,36,1151(in Chinese).(许健,宋秋玲,有机化学,2016,36,1151.)
[4]For some selected examples,please see:(a)Citta,A.;Folda,A.;Bindoli,A.;Pigeon,P.;Top,S.;Vessières,A.;Salmain,M.;Jaouen,G.;Rigobello,M.P.J.Med.Chem.2014,57,8849.(b)Tehfe,M.;Dumur,F.;Graff,B.;Gigmes,D.;Fouassier,J.;Lalevée,J.Macromolecules 2013,46,3332.(c)Mróz,W.;Villafiorita-Monteleone,F.;Pasini,M.;Grisci,G.;Paolino,M.;Razzano,V.;Cappelli,A.;Botta,C.Mater.Lett.2015,142,197.(d)Guerlin,A.;Dumur,F.;Dumas,E.;Miomandre,F.;Wantz,G.C.;Mayer,R.Org.Lett.2010,12,2382.
[5]Selected examples,please see:(a)Mosslemin,M.H.;Shams,N.;Esteghamat,H.;Anaraki-Ardakani,H.Chin.Chem.Lett.2013,24,1095.(b)Zhou,F.;Yang,M.;Lu,X.Org.Lett.2009,11,1405.(c)Bu,X.;Hong,J.;Zhou,X.Adv.Synth.Catal.2011,353,2111.(d)Jia,X.;Petrone,D.A.;Lautens,M.Angew.Chem.,Int.Ed.2012,51,9870.(e)Zeng,Z.;Ilies,L.;Nakamura,E.J.Am.Chem.Soc.2011,133,17638.(f)Huang,X.;Yang,X.;Song,R.;Li,J.J.Org.Chem.2014,79,1025.
[6]Ye,S.;Gao,K.;Zhou,H.;Yang X.;Wu,J.Chem.Commun.2009,5406.
[7]Zhou,P.;Liu,W.;Qiu,H.Chem.Lett.2015,44,1637.
[8](a)Shi,Z.;Zhang,C.;Li,S.;Pan,D.Ding,S.;Cui,Y.;Jiao,N.Angew.Chem.,Int.Ed.2009,48,4572.(b)Lafrance,M.;Fagnou,K.J.Am.Chem.Soc.2006,128,16496.
[9]Zhou,F.;Han,X.;Lu,X.J.Org.Chem.2011,76,1491.
[2]Selected examples on chloropalladation with Cu Cl2:(a)Huang,J.;Dong,Y.;Wang,X.;Luo,H.Chem.Commun.2010,46,1035.(b)An,Y.;Li,J.;Zhang,Z.;Li,C.;Yang,S.Chin.J.Org.Chem.2016,36,2136(in Chinese).(安艳妮,李建晓,张振明,李春生,杨少容,有机化学,2016,36,2136.)(c)Li,J.;Li,C.;Yang,S.;Luo,W.Chin.J.Org.Chem.2015,35,898(in Chinese).(李建晓,李春生,杨少容,罗维,有机化学,2015,35,898.)
[3]Review on the reactions with O2:(a)Wu,W.;Jiang,H.Acc.Chem.Res.2012,45,1736.(b)Wu,W.;Jiang,H.Acc.Chem.Res.2014,47,2483.(c)Wu,K.;Song,C.;Cui,D.Chin.J.Org.Chem.2017,37,586(in Chinese).(吴空,宋婵,崔冬梅,有机化学,2017,37,586.)(d)Cheng,X.;Hu,X.;Lu,Z.Chin.J.Org.Chem.2017,37,251(in Chinese).(程骁恺,胡新根,陆展,有机化学,2017,37,251.)(e)Xu,J.;Song,Q.Chin.J.Org.Chem.2016,36,1151(in Chinese).(许健,宋秋玲,有机化学,2016,36,1151.)
[4]For some selected examples,please see:(a)Citta,A.;Folda,A.;Bindoli,A.;Pigeon,P.;Top,S.;Vessières,A.;Salmain,M.;Jaouen,G.;Rigobello,M.P.J.Med.Chem.2014,57,8849.(b)Tehfe,M.;Dumur,F.;Graff,B.;Gigmes,D.;Fouassier,J.;Lalevée,J.Macromolecules 2013,46,3332.(c)Mróz,W.;Villafiorita-Monteleone,F.;Pasini,M.;Grisci,G.;Paolino,M.;Razzano,V.;Cappelli,A.;Botta,C.Mater.Lett.2015,142,197.(d)Guerlin,A.;Dumur,F.;Dumas,E.;Miomandre,F.;Wantz,G.C.;Mayer,R.Org.Lett.2010,12,2382.
[5]Selected examples,please see:(a)Mosslemin,M.H.;Shams,N.;Esteghamat,H.;Anaraki-Ardakani,H.Chin.Chem.Lett.2013,24,1095.(b)Zhou,F.;Yang,M.;Lu,X.Org.Lett.2009,11,1405.(c)Bu,X.;Hong,J.;Zhou,X.Adv.Synth.Catal.2011,353,2111.(d)Jia,X.;Petrone,D.A.;Lautens,M.Angew.Chem.,Int.Ed.2012,51,9870.(e)Zeng,Z.;Ilies,L.;Nakamura,E.J.Am.Chem.Soc.2011,133,17638.(f)Huang,X.;Yang,X.;Song,R.;Li,J.J.Org.Chem.2014,79,1025.
[6]Ye,S.;Gao,K.;Zhou,H.;Yang X.;Wu,J.Chem.Commun.2009,5406.
[7]Zhou,P.;Liu,W.;Qiu,H.Chem.Lett.2015,44,1637.
[8](a)Shi,Z.;Zhang,C.;Li,S.;Pan,D.Ding,S.;Cui,Y.;Jiao,N.Angew.Chem.,Int.Ed.2009,48,4572.(b)Lafrance,M.;Fagnou,K.J.Am.Chem.Soc.2006,128,16496.
[9]Zhou,F.;Han,X.;Lu,X.J.Org.Chem.2011,76,1491.