第5期 莫凡洋,张艳,王剑波:芳香碳氢键的活化官能化研究进展 325 2] ALBERICO D, SCOTT M E, LAUTENS M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [].Chem Rev,2007,107(2):174-238 3] TSUJI J. Palladium Reagents and Catalysts [M]. New York: Wiley Sons, 1995 4] JIA C, KITAMURA T, FUJIWARA Y. Catalytic functionalization of arenes and Alkanes via C-H bond activation D]. Acc Chem Res,2001,34(8):633-639 5] JIA C, PIAO D, OYAMADA J, et al. Efficient activation of aromatic C-H bonds for addition to C-C multiple Bonds [] ence,2000,287(5460):1992-1995 6] STAHL SS. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct Dioxygen -coupled turnover [].An- gew Chem Int ed,2004,43(26):3400-3420 [] MORITANI I, FUJIWARA Y. Aromatic substitution of styrene -palladium chloride complex []. Tetrahedron Lett, 1967, 8(12) l119-1122. 8] FUJIWARA Y, MORITANI I, DANNO S,et al. Aromatic substitution of olefins. VI. Arylation of olefins with palladium(II)ace- tate I. 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Palladium catalyzed direct arylation of(hetero)arenes with aryl boronic acids [].Angew Chem Int Ed,2008,47(8):1473-1476 [5] KAWAI H, KOBAYASHI Y, OI S,et al. Direct C-H bond arylation of arenes with aryltin reagents catalysed by palladium com- plexes]. Chem commun,2008,39(30):1464-1466 [6] VAN HELDEN R, VERBERG G. The oxidative coupling of aromatic compounds with palladium salts []. Recl Trav Chim Pays Bas,1965,84(10):1263-1273 [17] STUART D R, FAGNOU K. The catalytic cross -coupling of unactivated arenes D]. Science, 2007, 316(5828): 1 172-1175 [8] STUART D R, VILLEMURE E, FAGNOU K. Elements of regiocontrol in palladium-catalyzed oxidative arene cross -coupling D]. J Am Chem Soc,2007,129(40):12072-12073 [9] HULL K L, SANFORD M S. Catalytic and highly regioselective cross - coupling of aromatic C-H substrates []. J Am Chem Soe,2007,129(39):11904-11905 20] LI B J, TIAN S L, FANG Z,et al. Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components []. Angew Chem Int Ed, 2008,47(6): 1 115-1 118 [21] SATOH T, KAWAMURA Y, MIURA M, et al. Palladium-catalyzed regioselective mono-and diarylation reactions of 2-pheny- Phenols and naphthols with aryl halides []. Angew Chem Int Ed, 1997, 36(16): 1740-1742 22] KALYANI D, DEPREZ N R, DESAI L V,et al. Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights [].J Am Chem Soc, 2005, 127(20): 7330-7331 23] LAFRANCE M, FAGNOU K. Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design []. J Am Chem Soc, 2006, 128(51): 16496-14697 24] YAN G, KUANG C, ZHANG Y, et al. Palladium-catalyzed direct cyanation of indoles with K Fe(cn).] 0]. Org Lett, 2010 12(5):1052-1055 25] MURAI S, KAKIUCHI F, SEKINE S,et al. Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins [].Na ture,1993,366(6455):529-531 6 KAKIUCHI E KAN S IGI K, et alo A ruthenium o catalyzed reaction f aromatic ke J Am Chem Soc,2003,125(7):1698-1670［2］ ALBERICO D，SCOTT M E，LAUTENS M． Aryl － aryl bond formation by transition － metal － catalyzed direct arylation［J］． Chem Rev，2007，107( 2) : 174 － 238． ［3］ TSUJI J． Palladium Reagents and Catalysts ［M］． New York: Wiley ＆ Sons，1995． ［4］ JIA C，KITAMURA T，FUJIWARA Y． Catalytic functionalization of arenes and Alkanes via C—H bond activation［J］． Acc Chem Res，2001，34( 8) : 633 － 639． ［5］ JIA C，PIAO D，OYAMADA J，et al． Efficient activation of aromatic C—H bonds for addition to C － C multiple Bonds ［J］． Sci￾ence，2000，287( 5460) : 1 992 － 1 995． ［6］ STAHL S S． Palladium oxidase catalysis: selective oxidation of organic chemicals by direct Dioxygen － coupled turnover［J］． An￾gew Chem Int Ed，2004，43( 26) : 3 400 － 3 420． ［7］ MORITANI I，FUJIWARA Y． Aromatic substitution of styrene － palladium chloride complex［J］． Tetrahedron Lett，1967，8( 12) : 1 119 － 1 122． ［8］ FUJIWARA Y，MORITANI I，DANNO S，et al． Aromatic substitution of olefins． VI． Arylation of olefins with palladium( II) ace￾tate ［J］． J Am Chem Soc，1969，91( 25) : 7 166 － 7 169． ［9］ CHEN X，GOODHUE C E，YU J Q． Palladium － catalyzed alkylation of sp2 and sp3 C—H bonds with methylboroxine and alkylbo￾ronic acids: two distinct C—H activation pathways ［J］． J Am Chem Soc，2006，128( 36) : 12 634 － 12 635． ［10］ GIRI R，MAUGEL N，LI J J，et al． Palladium － catalyzed methylation and Arylation of sp2 and sp3 C—H bonds in simple carbox￾ylic acids［J］． J Am Chem Soc，2007，129( 12) : 3 510 － 3 511． ［11］ WANG D H，MEI T S，YU J Q． Versatile Pd( II) － Catalyzed C—H activation /aryl － aryl coupling of benzoic and phenyl acetic acids［J］． J Am Chem Soc，2008，130( 52) : 17 676 － 17 677． ［12］ YANG S D，LI B J，WAN X B，et al． Ortho arylation of acetanilides via Pd( Ⅱ) － catalyzed C—H functionalization ［J］． J Am Chem Soc，2007，129( 19) : 6 066 － 6 067． ［13］ SHI Z J，LI B J，WAN X B，et al． Suzuki － miyaura coupling reaction by Pd( Ⅱ) － catalyzed aromatic C—H bond activation di￾rected by an N － alkyl acetamino group ［J］． Angew Chem Int Ed，2007，46( 29) : 5 554 － 5 558． ［14］ YANG S D，SUN C L，FANG Z，et al． Palladium catalyzed direct arylation of ( hetero) arenes with aryl boronic acids［J］． Angew Chem Int Ed，2008，47( 8) : 1 473 － 1 476． ［15］ KAWAI H，KOBAYASHI Y，OI S，et al． Direct C—H bond arylation of arenes with aryltin reagents catalysed by palladium com￾plexes ［J］． Chem Commun，2008，39( 30) : 1 464 － 1 466． ［16］ VAN HELDEN R，VERBERG G． The oxidative coupling of aromatic compounds with palladium salts［J］． Recl Trav Chim Pays － Bas，1965，84( 10) : 1 263 － 1 273． ［17］ STUART D R，FAGNOU K． The catalytic cross － coupling of unactivated arenes［J］． Science，2007，316( 5828) : 1 172 － 1 175． ［18］ STUART D R，VILLEMURE E，FAGNOU K． Elements of regiocontrol in palladium － catalyzed oxidative arene cross － coupling ［J］． J Am Chem Soc，2007，129( 40) : 12 072 － 12 073． ［19］ HULL K L，SANFORD M S． Catalytic and highly regioselective cross － coupling of aromatic C—H substrates ［J］． J Am Chem Soc，2007，129( 39) : 11 904 － 11 905． ［20］ LI B J，TIAN S L，FANG Z，et al． Multiple C—H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components ［J］． Angew Chem Int Ed，2008，47( 6) : 1 115 － 1 118． ［21］ SATOH T，KAWAMURA Y，MIURA M，et al． Palladium － catalyzed regioselective mono － and diarylation reactions of 2 － pheny￾lphenols and naphthols with aryl halides ［J］． Angew Chem Int Ed，1997，36( 16) : 1 740 － 1 742． ［22］ KALYANI D，DEPREZ N R，DESAI L V，et al． Oxidative C—H activation /C—C bond forming reactions: synthetic scope and mechanistic insights ［J］． J Am Chem Soc，2005，127( 20) : 7 330 － 7 331． ［23］ LAFRANCE M，FAGNOU K． Palladium － catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design ［J］． J Am Chem Soc，2006，128( 51) : 16 496 － 14 697． ［24］ YAN G，KUANG C，ZHANG Y，et al． Palladium － catalyzed direct cyanation of indoles with K4［Fe( CN) 6］［J］． Org Lett，2010， 12( 5) : 1 052 － 1 055． ［25］ MURAI S，KAKIUCHI F，SEKINE S，et al． Efficient catalytic addition of aromatic carbon － hydrogen bonds to olefins ［J］． Na￾ture，1993，366( 6455) : 529 － 531． ［26］ KAKIUCHI F，KAN S，IGI K，et al． A ruthenium － catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C—H bond cleavage ［J］． J Am Chem Soc，2003，125( 7) : 1 698 － 1 670． 第 5 期 莫凡洋，张 艳，王剑波: 芳香碳氢键的活化官能化研究进展 325