过渡金属催化烯烃串联反应合成3,3-双取代吲哚酮的研究进展
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摘要
3,3-双取代吲哚酮类化合物具有良好的生理及生物活性,关于此类化合物的合成及应用报道越来越多。本文综述了近几年过渡金属催化烯烃串联反应这一合成方法在3,3-双取代吲哚酮合成中的应用,结合本课题组的工作,总结这类反应的机理,并对其发展前景进行展望。
The oxindole derivatives disubstituted at the C-3 position often exhibit excellent physiological activities and bioactivities. This review summarizes the recent advances of the access to 3,3-disubstituted indolinones via the strategy of transition-metal catalyzed cascade reaction of olefins. We also discussed the mechanism of these reactions by combining with our group's work and prospected the development of the synthetic methods.
The oxindole derivatives disubstituted at the C-3 position often exhibit excellent physiological activities and bioactivities. This review summarizes the recent advances of the access to 3,3-disubstituted indolinones via the strategy of transition-metal catalyzed cascade reaction of olefins. We also discussed the mechanism of these reactions by combining with our group's work and prospected the development of the synthetic methods.
引文
[1]张和智,欧阳贵平,陈洪,等.2-吲哚酮类化合物的研究进展[J].精细化工中间体,2016,46(1):10-14.
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[9]Liu X,Ma X,Huang Y,et al.Pd-catalyzed Heck-type cascade reactions with N-tosyl hydrazones:An efficient way to alkenes via in situ generated alkylpalladium[J].Org Lett,2013,15(18):4814-4817.
[10]Wu T,Mu A,Liu G.Palladium-catalyzed oxidative arylalkylation of activated alkenes:dual C-H bond cleavage of an arene and acetonitrile[J].Angew Chem Int Ed,2011,50(52):12578-12581.
[11]Mu X,Wu T,Liu G S.Palladium-catalyzed oxidative aryltrifluoromethylation of activated alkenes at room temperature[J].J Am Chem Soc,2012,134(2):878-881.
[12]Zhou S,Guo L,Wang H,et al.Copper-catalyzed oxidative benzylarylation of acrylamides by benzylic C-H bond functionalization for the synthesis of oxindoles[J].Chem Eur J,2013,19(39):12970-12973.
[13]Shi L,Wang Y,Yang H,et al.Copper-catalyzed bisarylations of alkenes leading to oxindole derivatives[J].Org Biomol Chem,2014,12(24):4070-4073.
[14]Li Z,Zhang Y,Zhang L,et al.Free-radical cascade alkylarylation of alkenes with simple alkanes:highly efficient access to oxindoles via selective(sp3)C-H and(sp2)C-H bond functionalization[J].Org Lett,2014,16(2):382-385.
[15]Lu Q,Liu C,Peng P,et al.Copper-catalyzed trifluoromethylation-initiated radical oxidative annulation toward oxindoles[J].Asian J Org Chem,2014,3(3):273-276.
[16]Wang R H,Bao W L.Copper promoted radical addition/cyclization of azobisisobutyronitrile with alkenes:a convenient process to synthesize 3-(2'-cyano alkyl)oxindoles[J].RSC Adv,2015,5:57469-57471.
[17]Yuan Y,Shen T,Jiao N.Ag-promoted azidocarbocyclization of activated alkenes via C-H bond cleavage[J].Chem Asian J,2013,8(12):2932-2935.
[18]Wei Xiaohong,Li Yamin,Zhou Anxi,et al.Silver-catalyzed carboazidation of arylacrylamides[J].Org Lett,2013,15(16):4158-4161.
[19]Wang H,Guo L,Duan X.Silver-catalyzed oxidative coupling/cyclization of acrylamides with 1,3-dicarbonyl compounds[J].Chem Commun,2013,49(88):10370-10372.
[20]Yin Feng,Wang Xisheng.Silver-mediated radical aryltrifluoromethylthiolation of activated alkenes[J].Org Lett,2014,16(4):1128-1131.
[21]Li Y M,Sun M,Wang H L,et al.Direct annulations toward phosphorylated oxindoles:silver-catalyzed carbonphosphorus functionalization of alkenes[J].Angew Chem Int Ed,2013,52(14):3972-3976.
[22]Wei W T,Zhou M B,Fan J H,et al.Synthesis of oxindoles by iron-catalyzed oxidative 1,2-alkylarylation of activated alkenes with an aryl C(sp2)-H bond and a C(sp3)-Hbond adjacent to a heteroatom[J].Angew Chem Int Ed,2013,52(13):3638-3641.
[23]Shen T,Yuan Y,Song S,et al.Iron-catalyzed aerobic difunctionalization of alkenes:a highly efficient approach to construct oxindoles by C-S and C-C bond formation[J].Chem Commun,2014,50(31):4115-4118.
[24]Dai Q,Yu J,Jiang Y,et al.The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization[J].Chem Commun,2014,50(29):3865-3867.
[25]Lu M Z,Loh T P.Iron-catalyzed cascade carbochloromethylation of activated alkenes:highly efficient access to chloro-containing oxindoles[J].Org Lett,2014,16(18):4698-4701.
[26]Wang R H,Bao W L.Iron(III)acetylacetonate catalyzed tandem oxidative addition/cyclization of simple amides with alkenes:a convenient process to synthesize 3-amido oxindoles[J].Tetrahedron,2015,71:6997-7002.
[27]Cui Zhihao,Du Daming.Decarboxylative synthesis of functionalized oxindoles via an iron-initiated radical chain process and application in constructing diverse fusedindoline heterocycles[J].Adv Synth Catal,2018,360(1):93-99.
[28]Xie Z G,Li P H,Wang L.Visible-light-induced and ironcatalyzed methylation of N-arylacrylamides with dimethyl sulphoxide:a convenient access to 3-ethyl-3methyl oxindoles[J].Org Biomol Chem,2017,15(19):4205-4211.
[29]Xu S M,Chen J Q,Xu P F.Aroyl chlorides as novel acyl radical precursors via visible-light photoredox catalysis[J].Org Chem Front,2017,4:1331-1335.
[2]Jensen B S.BMS-204352:a potassium channel opener developed for the treatment of stroke[J].CNS Drug Rev,2002,8(4):353-360.
[3]Galliford C V,Scheidt K A.Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents[J].Angew Chem Int Ed,2007,46:8748-8758.
[4]Alper P,Meyers C,Carreira E M.Facile,novel methodology for the synthesis of spiro[pyrrolidin-3,3'-oxindoles]:catalyzed ring expansion reactions of cyclopropanes by aldimines[J].Angew Chem Int Ed,1999,38(21):3186-3189.
[5]Marti C,Carreira E M.Construction of spiro[pyrrolidine3,3-oxindoles]recent applications to the synthesis of oxindole alkaloids[J].European Journal of Organic Chemistry,2003,124:2209-2219.
[6]Taylor A,Altmanand R,Buchwald S L.Palladium-catalyzed enantioselectiveα-arylation andα-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand[J].J Am Chem Soc,2009,131(29):9900-9901.
[7]Shen K,Liu X H,Feng X M.Recent progress in enantioselective synthesis of C3-functionalized oxindoles:rare earth metals take action[J].Chem Sci,2012,3(2):327-334.
[8]Pinto A,Jia Y,Neuville L,et al.Palladium-catalyzed enantioselective domino Heck-cyanation sequence:development and application to the total synthesis of esermethole and physostigmine[J].Chem Eur J,2007,13(3):961-967.
[9]Liu X,Ma X,Huang Y,et al.Pd-catalyzed Heck-type cascade reactions with N-tosyl hydrazones:An efficient way to alkenes via in situ generated alkylpalladium[J].Org Lett,2013,15(18):4814-4817.
[10]Wu T,Mu A,Liu G.Palladium-catalyzed oxidative arylalkylation of activated alkenes:dual C-H bond cleavage of an arene and acetonitrile[J].Angew Chem Int Ed,2011,50(52):12578-12581.
[11]Mu X,Wu T,Liu G S.Palladium-catalyzed oxidative aryltrifluoromethylation of activated alkenes at room temperature[J].J Am Chem Soc,2012,134(2):878-881.
[12]Zhou S,Guo L,Wang H,et al.Copper-catalyzed oxidative benzylarylation of acrylamides by benzylic C-H bond functionalization for the synthesis of oxindoles[J].Chem Eur J,2013,19(39):12970-12973.
[13]Shi L,Wang Y,Yang H,et al.Copper-catalyzed bisarylations of alkenes leading to oxindole derivatives[J].Org Biomol Chem,2014,12(24):4070-4073.
[14]Li Z,Zhang Y,Zhang L,et al.Free-radical cascade alkylarylation of alkenes with simple alkanes:highly efficient access to oxindoles via selective(sp3)C-H and(sp2)C-H bond functionalization[J].Org Lett,2014,16(2):382-385.
[15]Lu Q,Liu C,Peng P,et al.Copper-catalyzed trifluoromethylation-initiated radical oxidative annulation toward oxindoles[J].Asian J Org Chem,2014,3(3):273-276.
[16]Wang R H,Bao W L.Copper promoted radical addition/cyclization of azobisisobutyronitrile with alkenes:a convenient process to synthesize 3-(2'-cyano alkyl)oxindoles[J].RSC Adv,2015,5:57469-57471.
[17]Yuan Y,Shen T,Jiao N.Ag-promoted azidocarbocyclization of activated alkenes via C-H bond cleavage[J].Chem Asian J,2013,8(12):2932-2935.
[18]Wei Xiaohong,Li Yamin,Zhou Anxi,et al.Silver-catalyzed carboazidation of arylacrylamides[J].Org Lett,2013,15(16):4158-4161.
[19]Wang H,Guo L,Duan X.Silver-catalyzed oxidative coupling/cyclization of acrylamides with 1,3-dicarbonyl compounds[J].Chem Commun,2013,49(88):10370-10372.
[20]Yin Feng,Wang Xisheng.Silver-mediated radical aryltrifluoromethylthiolation of activated alkenes[J].Org Lett,2014,16(4):1128-1131.
[21]Li Y M,Sun M,Wang H L,et al.Direct annulations toward phosphorylated oxindoles:silver-catalyzed carbonphosphorus functionalization of alkenes[J].Angew Chem Int Ed,2013,52(14):3972-3976.
[22]Wei W T,Zhou M B,Fan J H,et al.Synthesis of oxindoles by iron-catalyzed oxidative 1,2-alkylarylation of activated alkenes with an aryl C(sp2)-H bond and a C(sp3)-Hbond adjacent to a heteroatom[J].Angew Chem Int Ed,2013,52(13):3638-3641.
[23]Shen T,Yuan Y,Song S,et al.Iron-catalyzed aerobic difunctionalization of alkenes:a highly efficient approach to construct oxindoles by C-S and C-C bond formation[J].Chem Commun,2014,50(31):4115-4118.
[24]Dai Q,Yu J,Jiang Y,et al.The carbomethylation of arylacrylamides leading to 3-ethyl-3-substituted indolin-2-one by cascade radical addition/cyclization[J].Chem Commun,2014,50(29):3865-3867.
[25]Lu M Z,Loh T P.Iron-catalyzed cascade carbochloromethylation of activated alkenes:highly efficient access to chloro-containing oxindoles[J].Org Lett,2014,16(18):4698-4701.
[26]Wang R H,Bao W L.Iron(III)acetylacetonate catalyzed tandem oxidative addition/cyclization of simple amides with alkenes:a convenient process to synthesize 3-amido oxindoles[J].Tetrahedron,2015,71:6997-7002.
[27]Cui Zhihao,Du Daming.Decarboxylative synthesis of functionalized oxindoles via an iron-initiated radical chain process and application in constructing diverse fusedindoline heterocycles[J].Adv Synth Catal,2018,360(1):93-99.
[28]Xie Z G,Li P H,Wang L.Visible-light-induced and ironcatalyzed methylation of N-arylacrylamides with dimethyl sulphoxide:a convenient access to 3-ethyl-3methyl oxindoles[J].Org Biomol Chem,2017,15(19):4205-4211.
[29]Xu S M,Chen J Q,Xu P F.Aroyl chlorides as novel acyl radical precursors via visible-light photoredox catalysis[J].Org Chem Front,2017,4:1331-1335.