摘要
以酰胺直接转化的C—C键形成方法为主线,简要回顾近年取得的主要突破.内容涵盖基于三氟甲磺酸酐活化、化学选择性试剂的还原官能化策略,以及两类催化转化.这些重要进展表明温和条件下的酰胺转化可达到优异的化学选择性、官能团容忍性和较好的底物普适性,转化产物还包括多种官能化的胺、酮和烯胺酯(酮)化合物等,并已在天然产物和生理活性化合物的合成中得到应用与检验.
Amides are a class of easily available compounds, and widely serve as versatile intermediates in organic synthesis and medicinal chemistry. Amide-based transformations could lead to many useful compounds and intermediates including various amines, ketones and enaminones. Though direct transformation of amides is of high demand, many current chemoselective transformations are only achieved in multistep approaches. In recent years, direct transformation of amides is emerging as an exciting area. A number of recent progresses on nucleophilic addition to amide carbonyl group that led to new C—C bond formation are highlighted in this review, including(1) in situ amide activation with trifluoromethanesulfonic anhydride(Tf_2O) followed by addition of π-and σ-nucleophiles or reactive organometallic reagents;(2) direct transformation of N-alkoxyamides;(3) direct transformation of amides using Schwartz reagent; and(4) catalytic reductive C—C bond forming reactions of amides, and metal catalyzed coupling of amides.
引文
[1]Brown,R.S.In The Amide Linkage:Structural Significance in Chemistry,Biochemistry,and Materials Science,Eds.:Greenberg,A.;Breneman,C.M.;Liebman,J.F.,John Wiley&Sons,Hoboken,2000,pp.85~114.
[2](a)Ma,X.Y.;An,X.T.;Zhao,X.H.;Du,J.Y.;Deng,Y.H.;Zhang,X.Z.;Fan,C.A.Org.Lett.2017,19,2965.(b)Shu,C.;Li,L.;Tan,T.D.;Yuan,D.Q.;Ye,L.W.Sci.Bull.2017,62,352.(c)Kong,D.Y.;Li,M.N.;Wang,R.;Zi,G.F.;Hou,G.H.Org.Biomol.Chem.2016,14,1216.(d)Li,Y.;Li,J.;Ding,H.F.;Li,A.Natl.Sci.Rev.2017,4,397.(e)Chen,W.;Zhang,H.B.Sci.China:Chem.2016,59,1065.(f)Yu,K.;Gao,B.L.;Ding,H.F.Acta Chim.Sinica 2016,74,410.(余宽,高北岭,丁寒锋,化学学报,2016,74,410)(g)Yu,X.Y.;Zhou,F.;Chen,J.R.;Xiao,W.J.Acta Chim.Sinica 2017,75,86.(余晓叶,周帆,陈加荣,肖文精,化学学报,2017,75,86.)
[3](a)Wu,Q.F.;Shen,P.X.;He,J.;Wang,X.B.;Zhang,F.;Shao,Q.;Zhu,R.Y.;Mapelli,C.;Qiao,J.X.;Poss,M.A.;Yu,J.Q.Science2017,355,499.(b)Kainz,Q.M.;Matier,C.D.;Bartoszewicz,A.;Zultanski,S.L.;Peters,J.C.;Fu,G.C.Science 2016,351,681.(c)Luo,F.H.;Long,Y.;Li,Z.K.;Zhou,X.G.Acta Chim.Sinica 2016,74,805.(罗飞华,龙洋,李正凯,周向葛,化学学报,2016,74,805.)
[4]For recent reviews,see:(a)Chardon,A.;Morisset,E.;Rouden,J.;Blanchet,J.Synthesis 2018,50,984.(b)Volkov,A.;Tinnis,F.;Slagbrand,T.;Trillo,P.;Adolfsson,H.Chem.Soc.Rev.2016,45,6685.(c)Zhang,L.L.;Han,Z.B.;Zhang,L.Li,M.X.;Ding,K.L.Chin.J.Org.Chem.2016,36,1824.(张琳莉,韩召斌,张磊,李明星,丁奎岭,有机化学,2016,36,1824.)(d)Smith,A.M.;Whyman,R.Chem.Rev.2014,114,5477.(e)Werkmeister,S.;Junge,K.;Beller,M.Org.Process Res.Dev.2014,18,289.(f)Addis,D.;Das,S.;Junge,K.;Beller,M.Angew.Chem.,Int.Ed.2011,50,6004.
[5]Seyden-Penne,J.Reductions by the Alumino-and Borohydrides in Organic Synthesis,2nd ed.,Wiley-VCH,New York,1997.
[6]Li,J.;Zhang,W.H.;Zhang,F.;Chen,Y.;Li,A.J.Am.Chem.Soc.2017,139,14893.correction:J.Am.Chem.Soc.2018,140,2384.
[7](a)Mateo,P.;Cinqualbre,J.;Mojzes,M.M.;Schenk,K.;Renaud,P.J.Org.Chem.2017,82,12318.See also:(b)Murai,T.;Mutoh,Y.;Ohta,Y.;Murakami,M.J.Am.Chem.Soc.2004,126,5968.For a review,see:(c)Murai,T.;Mutoh,Y.Chem.Lett.2012,41,2.
[8](a)Abels,F.;Lindemann,C.;Koch,E.;Schneider,C.Org.Lett.2012,14,5972.(b)Abels,F.;Lindemann,C.;Schneider,C.Chem.–Eur.J.2014,20,1964.
[9]Lee,A.S.;Liau,B.B.;Shair,M.D.J.Am.Chem.Soc.2014,136,13442.
[10]Michael,J.P.;de Koning,C.B.;Gravestock,D.;Hosken,G.D.;Howard,A.S.;Jungmann,C.M.;Krause,R.W.M.;Parsons,A.S.;Pelly,S.C.;Stanbury,T.V.Pure Appl.Chem.1999,71,979.
[11]Hussaini,S.R.;Chamala,R.R.;Wang,Z.Tetrahedron 2015,71,6017.
[12]For reviews,see:(a)Seebach,D.Angew.Chem.,Int.Ed.2011,50,96.(b)Pace,V.;Holzer,W.Aust.J.Chem.2013,66,507.(c)Pace,V.;Holzer,W.;Olofsson,B.Adv.Synth.Catal.2014,356,3697.(d)Sato,T.;Chida,N.Org.Biomol.Chem.2014,12,3147.(e)Kaiser,D.;Maulide,N.J.Org.Chem.2016,81,4421.(f)Sato,T.;Chida,N.J.Synth.Org.Chem.Jpn.2016,74,599.(g)Li,X.J.;Sun,Y.;Zhang L.;Peng,B.Chin.J.Org.Chem.2016,36,2530(李晓锦,孙艳,张磊,彭勃,有机化学,2016,36,2530).(h)Evano,G.;Lecomte,M.;Thilmany,P.;Theunissen,C.Synthesis 2017,49,3183.(i)Adachi,S.;Kumagai,N.;Shibasaki,M.Tetrahedron Lett.2018,59,1147.
[13](a)Stang,P.J.;White,M.R.Aldrichim.Acta 1983,16,15.(b)Baraznenok,I.L.;Nenajdenko,V.G.;Balenkova,E.S.Tetrahedron 2000,56,3077.For an excellent mechanistic investigation on the role of base additive in conjuction with Tf2O,see:(c)Mátrav?lgyi,B.;Hergert,T.;Bálint,E.;Bagi,P.;Faigl,F.J.Org.Chem.2018,83,2282.
[14](a)Falmagne,J.B.;Escudero,J.;Talebsahraoui,S.;Ghosez,L.Angew.Chem.Int.Ed.Engl.1981,20,879.(b)Chen,L.Y.;Ghosez,L.Tetrahedron Lett.1990,31,4467.
[15]Martinez,A.G.;Alvarez,R.M.;Barcina,J.O.;Cerero,S.M.;Vilar,E.T.;Fraile,A.G.;Hanack,M.;Subramanian,L.R.J.Chem.Soc.,Chem.Commun.1990,1571.
[16]Sisti,N.J.;Fowler,F.W.;Grierson,D.S.Synlett 1991,816.
[17]Banwell,M.G.;Cowden,C.J.;Gable,R.W.J.Chem.Soc.,Perkin Trans.1 1994,3515.
[18]Myers,A.G.;Tom,N.J.;Fraley,M.E.;Cohen,S.B.;Madar,D.J.J.Am.Chem.Soc.1997,119,6072.
[19](a)Magnus,P.;Gazzard,L.;Hobson,L.;Payne,A.H.;Lynch,V.Tetrahedron Lett.1999,40,5135.(b)Magnus,P.;Gazzard,L.;Hobson,L.;Payne,A.H.;Rainey,T.J.;Westlund,N.;Lynch,V.Tetrahedron 2002,58,3423.
[20](a)Bélanger,G.;Larouche-Gauthier,R.;Ménard,F.;Nantel,M.;Barabé,F.Org.Lett.2005,7,4431.(b)Bélanger,G.;Larouche-Gauthier,R.;Ménard,F.;Nantel,M.;Barabé,F.J.Org.Chem.2006,71,704.
[21](a)Movassaghi,M.;Hill,M.D.J.Am.Chem.Soc.2006,128,4592.(b)Movassaghi,M.;Hill,M.D.;Ahmad,O.K.J.Am.Chem.Soc.2007,129,10096.
[22]Hendrickson,J.B.;Hussoin,M.D.J.Org.Chem.1987,52,4137.
[23](a)You,S.L.;Razavi,H.;Kelly,J.W.Angew.Chem.,Int.Ed.2003,42,83;(b)You,S.-L.;Kelly,J.W.Org.Lett.2004,6,1681.
[24](a)Zhou,H.B.;Liu,G.S.;Yao,Z.J.Org.Lett.2007,9,2003.(b)Atia,M.;Bogdán,D.;Brügger,M.;Haider,N.;Mátyus,P.Tetrahedron 2017,73,3231.(c)Dong,Q.L.;Liu,G.S.;Zhou,H.B.;Chen,L.;Yao,Z.J.Tetrahedron Lett.2008,49,1636.
[25]Movassaghi,M.;Hill,M.D.Org.Lett.2008,10,3485.
[26]Cui,S.L.;Wang,J.;Wang,Y.G.J.Am.Chem.Soc.2008,130,13526.
[27]Medley,J.W.;Movassaghi,M.J.Org.Chem.2009,74,1341.
[28](a)White,K.L.;Mewald,M.;Movassaghi,M.J.Org.Chem.2015,80,7403.(b)Mewald,M.;Medley,J.W.;Movassaghi,M.Angew.Chem.,Int.Ed.2014,53,11634.
[29](a)Handbook of Grignard Reagents,Eds.:Silverman,G.S.;Rakita,P.E.,Marcel Dekker,New York,1996;(b)Grignard Reagent:New Developments,Ed.:Richey,H.G.Jr.,Wiley,Chichester,2000;(c)Main Group Metals in Organic Synthesis,Eds.:Yamamoto,H.;Oshima,K.,Wiley-VCH,Weinheim,2004;(d)Handbook of Functionalized Organometallics Application in Synthesis,Ed.:Knochel,P.,Wiley-VCH,Weinheim,2005;(e)Klatt,T.;Markiewicz,J.T.;S?mann,C.;Knochel,P.J.Org.Chem.2014,79,4253;(f)Bao,R.L.-Y.;Zhao,R.;Shi,L.Chem.Commun.2015,51,6884,correction:Chem.Commun.2015,51,9744.
[30](a)Foubelo,F.;Yus,M.Chem.Soc.Rev.2008,37,2620;(b)Chinchilla,R.;Nájera,C.;Yus,M.Tetrahedron 2005,61,3139;(c)The Chemistry of Organolithium Compounds,Eds.:Rappoport,Z.;Marek,I.,Wiley-VCH,Weinheim,2004.
[31](a)Xiao,K.-J.;Luo,J.-M.;Ye,K.-Y.;Wang,Y.;Huang,P.-Q.Angew.Chem.,Int.Ed.2010,49,3037.(b)Huo,H.-H.;Luo,J.-M.;Xia,X.-E.;Zhang,H.-K.;Wang,Y.;Huang,P.-Q.Chem.Eur.J.2013,19,13075.
[32](a)Xiao,K.-J.;Wang,Y.;Ye,K.-Y.;Huang,P.-Q.Chem.Eur.J.2010,16,12792.(b)Xiao,K.-J.;Wang,Y.;Huang,Y.-H.;Wang,X.-G.;Huang,P.-Q.J.Org.Chem.2013,78,8305.
[33](a)Guérot,C.;Tchitchanov,B.H.;Knust,H.;Carreira,E.M.Org.Lett.2011,13,780.(b)Lindemann,C.;Schneider,C.Synthesis2016,48,828.
[34](a)Huo,H.-H.;Xia,X.-E.;Zhang,H.-K.;Huang,P.-Q.J.Org.Chem.2013,78,455.(b)Huang,P.-Q.;Geng,H.;Tian,Y.-S.;Peng,Q.-R.;Xiao,K.-J.Sci.China:Chem.2015,58,478.
[35]Bechara,W.S.;Pelletier,G.;Charette,A.B.Nat.Chem.2012,4,228.
[36](a)Xiao,K.-J.;Wang,A.-E;Huang,Y.-H.;Huang,P.-Q.Asian J.Org.Chem.2012,1,130.(b)Huang,P.-Q.;Huang,Y.-H.;Geng,H.;Ye,J.-L.Sci.Rep.2016,6,28801.(c)Huang,P.-Q.;Huang,Y.-H.Chin.J.Chem.2017,35,613.
[37]Xiao,K.-J.;Wang,A.-E;Huang,P.-Q.Angew.Chem.Int.Ed.2012,51,8314.
[38]Huang,P.-Q.;Ou,W.;Xiao,K.-J.;Wang,A.-E Chem.Commun.2014,50,8761.
[39]Huang,P.-Q.;Wang,Y.;Xiao,K.-J.;Huang,Y.-H.Tetrahedron 2015,71,4248.
[40](a)Castoldi,L.;Holzer,W.;Langer,T.;Pace,V.Chem.Commun.2017,53,9498.(b)Pace,V.;Murgia,I.;Westermayer,S.;Langer,T.;Holzer,W.Chem.Commun.2016,52,7584.
[41](a)Shirokane,K.;Kurosaki,Y.;Sato,T.;Chida,N.Angew.Chem.Int.Ed.2010,49,6369.(b)Yoritate,M.;Meguro,T.;Matsuo,N.;Shirokane,K.;Kurosaki,Y.;Sato,T.;Chida,N.Chem.Eur.J.2014,20,8210.See also:(c)Jaekel,M.;Qu,J.;Schnitzer,T.;Helmchen,G.Chem.Eur.J.2013,19,16746.
[42](a)Vincent,G.;Guillot,R.;Kouklovsky,C.Angew.Chem.Int.Ed.2011,50,1350.(b)Vincent,G.;Karila,D.;Khalil,G.;Sancibrao,P.;Gori,D.;Kouklovsky,C.Chem.-Eur.J.2013,19,9358.
[43](a)Schedler,D.J.A.;Godfrey,A.G.;Ganem,B.Tetrahedron Lett.1993,34,5035.(b)Schedler,D.J.A.;Li,J.;Ganem,B.J.Org.Chem.1996,61,4115.(c)Xia,Q.;Ganem,B.Org.Lett.2001,3,485.
[44](a)Nakajima,M.;Oda,Y.;Wada,T.;Minamikawa,R.;Shirokane,K.;Sato,T.;Chida,N.Chem.Eur.J.2014,20,17565.(b)Oda,Y.;Sato,T.;Chida,N.Org.Lett.2012,14,950.(c)Shirokane,K.;Wada,T.;Yoritate,M.;Minamikawa,R.;Takayama,N.;Sato,T.;Chida,N.Angew.Chem.Int.Ed.2014,53,512.(d)Fukami,Y.;Wada,T.;Meguro,T.;Chida,N.;Sato,T.Org.Biomol.Chem.2016,14,5486.(e)Shirokane,K.;Tanaka,Y.;Yoritate,M.;Takayama,N.Sato,T.;Chida,N.Bull.Chem.Soc.Jpn.2015,88,522.See also:(f)Pace,V.;Vega-Hernández,K.de la;Urban,E.;Langer,T.Org.Lett.2016,18,2750.
[45]Wi?c?aw,M.M.;Stecko,S.Eur.J.Org.Chem.2018,DOI:10.1002/ejoc.201701537
[46]Motoyama,Y.;Aoki,M.;Takaoka,N.;Aoto,R.;Nagashima,H.Chem.Commun.2009,1574.
[47](a)Gregory,A.W.;Chambers,A.;Hawkins,P.;Jakubec,A.;Dixon,D.J.Chem.-Eur.J.2015,21,111.(b)Tan,P.W.;Seayad,J.;Dixon,D.J.Angew.Chem.Int.Ed.2016,55,13436.
[48](a)Nakajima,M.;Sato,T.;Chida,N.Org.Lett.2015,17,1696.(b)Katahara,S.;Kobayashi,S.;Fujita,K.;Matsumoto,T.;Sato,T.;Chida,N.J.Am.Chem.Soc.2016,138,5246.(c)Katahara,S.;Kobayashi,S.;Fujita,K.;Matsumoto,T.;Sato,T.;Chida,N.Bull.Chem.Soc.Jpn.2017,90,893.
[49]Huang,P.-Q.;Ou,W.;Han,F.Chem.Commun.2016,52,11967.
[50](a)Fuentes de Arriba,A.L.;Lenci,E.;Sonawane,M.;Formery,O.;Dixon,D.J.Angew.Chem.Int.Ed.2017,56,3655.(b)Xie,L.G.;Dixon,D.J.Chem.Sci.2017,8,7492.
[51](a)Tinnis,F.;Volkov,A.;Slagbrand,T.;Adolfsson,H.Angew.Chem.,Int.Ed.2016,55,4562.(b)Slagbrand,T.;Kervefors,G.;Tinnis.F.;Adolfsson,H.Adv.Synth.Catal.2017,359,1990.(c)Trillo,P.;Slagbrand,T.;Tinnis F.;Adolfsson,H.Chem.Commun.2017,53,9159.
[52]Hie,L.;Fine Nathel,N.F.;Shah,T.;Baker,E.L.;Hong,X.;Yang,Y.F.;Liu,P.;Houk,K.N.;Garg,N.K.Nature 2015,524,79.
[53]Ritter,S.K.Chem.Eng.News 2015,93(49),23.
[54](a)Ritter,S.K.Chem.Eng.News Archive 2015,93(30),9.(b)Ruider,S.A.;Maulide,N.Angew.Chem.Int.Ed.2015,54,13856.
[55]Weires,N.A.;Baker,E.L.;Garg,N.K.Nat.Chem.2016,8,75.
[56]Meng,G.;Szostak,R.;Szostak,M.Org.Lett.2017,19,3596.
[57]Huang,P.-Q.;Chen,H.Chem.Commun.2017,53,12584.
[58](a)Kaiser,D.;Teskey,C.J.;Adler,P.;Maulide,N.J.Am.Chem.Soc.2017,139,16040.(b)Shaaban,S.;Tona,V.;Peng,B.;Maulide,N.Angew.Chem.Int.Ed.2017,56,10938.(c)Torre,A.;Kaiser,D.;Maulide,N.J.Am.Chem.Soc.2017,139,6578.(d)Kaiser,D.;de la Torre,A.;Shaaban,S.;Maulide,N.Angew.Chem.,Int.Ed.2017,56,5921.(e)Mauro,G.D.;Maryasin,B.;Kaiser,D.;Shaaban,S.;González,L.;Maulide,N.Org.Lett.2017,19,3815.(f)Tona,V.;Maryasin,B.;de la Torre,A.;Sprachmann,J.;González,L.;Maulide,N.Org.Lett.2017,19,2662.(g)Gawali,V.S.;Simeonov,S.;Drescher,M.;Knott,T.;Scheel,O.;Kudolo,J.;K?hlig,H.;Hochenegg,K.;Hochenegg,U.;Roller,A.;Todt,H.;Maulide,N.Chem Med Chem2017,12,1819.(h)Peng,B.;Geerdink,D.;Fares,C.;Maulide,N.Angew.Chem.Int.Ed.2014,53,5462.
[59](a)Xiao,P.H.;Tang,Z.X.;Wang,K.;Chen,H.;Guo,Q.Y.;Chu,Y.;Gao,L.;Song,Z.L.J.Org.Chem.2018,83,1687.(b)Li,L.H.;Niu,Z.J.;Liang,Y.M.Chem.Eur.J.2017,23,15300.(c)Li,X.W.;Lin,F.G.R.;Huang,K.M.;Wei,J.L.;Li,X.Y.;Wang,X.Y.;Geng,X.Y.;Jiao,N.Angew.Chem.Int.Ed.2017,56,12307.(d)Xie,C.M.;Luo,J.S.;Zhang,Y.;Zhu,L.L.;Hong,R.Org.Lett.2017,19,3592.(e)Chen,J.J.;Long,W.H.;Fang,S.W.;Yang,Y.G.;Wan,X.B.Chem.Commun.2017,53,13256.(f)Ding,G.N.;Wu,X.Y.;Jiang,L.L.;Zhang,Z.G.;Xie,X.M.Org.Lett.2017,19,6048.(g)Zhang,Q.;Yuan,J.W.;Yu,M.F.;Zhang,R.;Liang,Y.J.;Huang,P.;Dong,D.W.Synthesis 2017,49,4996.(h)Jiang Meng,J.;Jia,R.;Leng,J.;Wen,M.;Yu,X.;Deng,W.-P.Org.Lett.2017,19,4520.(i)Shi,L.;Tan,X.;Long,J.;Xiong,X.;Yang,S.;Xue,P.;Lv,H.;Zhang,X.Chem.-Eur.J.2017,23,546.(j)Yuan,M.L.;Xie,J.H.;Zhou,Q.L.Chem Cat Chem 2016,8,3036.(k)Yuan,M.L.;Xie,J.H.;Zhu,S.F.;Zhou,Q.L.ACS Catal.2016,6,3665.(l)Xing,S.Y.;Ren,J.;Wang,K.;Cui,H.;Xia,T.;Zhang,M.;Wang,D.D.Adv.Synth.Catal.2016,358,3093.(m)Lang,Q.-W.;Hu,X.-N.;Huang,P.-Q.Sci.China:Chem.2016,59,1638.(n)Mou,X.Q.;Xu,L.;Wang,S.H.;Yang,C.Tetrahedron Lett.2015,56,2820.(o)Zhang,T.X.;Zhang,Y.;Zhang,W.X.;Luo,M.-M.Adv.Synth.Catal.2013,355,2775.(p)Xie,W.;Zhao,M.;Cui,C.Organometallics 2013,32,7440.(q)Zhao,M.N.;Ren,Z.H.;Wang,Y.Y.;Guan,Z.H.Chem.Commun.2012,48,8105.