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Imprimatur:Date, SignatureSynthesisSynthesisReviews and Full Papersin Chemical SynthesisRecent Advances in Photocatalytic C–N Bond Coupling Reactions10/1/202020Vol. 52, No. 20October IIReview2899Synthesis 2020, 52, 2899–2921DOI: 10.1055/s-0040-1707136C.-M. ChanY.-C. ChowW.-Y. Yu*The Hong Kong Polytechnic University, Hong KongSynthesisSynthesis 2020, 52, 2922–2939DOI: 10.1055/s-0040-1707207A. CalcatelliA. Cherubini-CelliE. CarlettiX. Companyó*University of Padova, ItalyUnconventional Transformations of Morita–Baylis–Hillman AdductsShort Review2922This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.tc2020ss.fm
VISynthesisSynthesis 2020, 52, 2940–2947DOI: 10.1055/s-0040-1706403Titanocene-Catalyzed Regiodivergent Epoxide Opening – From Desymmetrizing meso-Epoxides to Regiodivergent Arylation of EpoxidesH. WeißbarthF. MühlhausA. Gansäuer*Universität Bonn, GermanyOROORH-Atom OTBS2940OHROXORShort veCatalyst controlledNOHR'SynthesisSynthesis 2020, 52, 2948–2961DOI: 10.1055/s-0040-1707210Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis ofHeterocyclesShort Review2948F. ZhaoD. MasciE. TomarelliD. Castagnolo*King’s College London, UKSynthesisSynthesis 2020, 52, 2962–2969DOI: 10.1055/s-0040-1707194M. DebiaisJ.-J. VasseurS. MüllerM. Smietana*University of Montpellier, CNRS,ENCSM, FranceSelective Chemical Modification of DNA with Boronic Acids byOn-Column CuAAc ReactionsFeature2962This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.R
VIISynthesis 2020, 52, 2970–2978DOI: 10.1055/s-0040-1707886F. SouquetW. DriciS. A. FayssalI. LazouniS. ThueillonJ. Pérard-Viret*Université de Paris, CiTCoM,FranceSynthesisSynthesis 2020, 52, 2979–2986DOI: 10.1055/s-0040-1707205Y.-X. WangY.-N. LuL.-L. XuF.-T. ShengJ.-P. Zhang*W. Tan*F. Shi*N-Acyliminium Ion Chemistry: Improving the Access to Unsaturated -Lactams and Their N- -Methoxylated Derivatives: Application to anExpeditive Synthesis of ( )-Crispine AOMeO1) R-NH2, HCl (1 M),40 C2) Na2HPO4OMeRSynthesis 2020, 52, 2987–3000DOI: 10.1055/s-0040-1707897M. DobeschJ. GreinerG. Maas*NO2970RNO69–91%7 examples39–78%8 examplesR-NH2 allylamine, aniline, benzylamine, thanamine, L-Lys(Z)-OMe,L-Phe-OMe, L-Val-OMeApplication of Benzofuran-Derived Azadienes as Two-Carbon BuildingBlocks in Annulations: Chemo- and Diastereoselective Construction ofSpiro-Benzofuran ScaffoldsPaper2979OHOt-But-But-But-BuNTsbase OO(2 4) annulationArRNTsROOHAr16 examplesup to 97% yield, 95:5 drJiangsu Normal University,P. R. of ChinaXuzhou Medical University,P. R. of ChinaSynthesisMeOHHCl (12 M; 2 equiv)r.t., 4 hOMeORNPSPTetrasubstituted Furans by Nucleophile-Induced Cleavage ofCarbonyl Ylide–DMAD CycloadductsCOOMeCOOMeMeOOCMeOOCCOOEtOUlm University, GermanyNOHNONuROOcat. Rh2(OAc)4DMADOONOCOOEtNu-HOCOOEtRN2RR H, Me, i-PrNu-H H2O, ROH, RS–/H ,NH3, 1 and 2 aminesPaper2987This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Synthesis
VIIISynthesis 2020, 52, 3001–3006DOI: 10.1055/s-0040-1707899An Efficient Copper-Catalyzed C(sp2)–S Formation Starting from ArylIodides and Tetramethylthiuram Monosulfide (TMTM)SIFGN SSCuCl (10 mol%)K2CO3 (1.0 equiv)NTMTMSynthesiswide substrate scopecost-effective substratessimple operationgood to excellent yields16 examplesyield: 71–97%R2R1Osaka City University, JapanBu3SnPaper3007Paracentrone(R1 OH, R2 Me)O19-Hexanoyloxyparacentrone 3-acetate(R1 AcO,R2 OBNR3OIR4OOOB OOIR4R4R3, R4 H or MeSynthesis 2020, 52, 3018–3028DOI: 10.1055/s-0040-1707895NSSynthesis of Allene-Containing Apocarotenoids by Cross-CouplingStrategyK. Sakaguchi*Y. NishiokaN. KinashiN. YukihiraT. ShinadaT. NishimuraH. HashimotoS. KatsumuraSynthesisSFGDMSO, 120 CtetramethylthiurammonosulfideSynthesis 2020, 52, 3007–3017DOI: 10.1055/s-0040-17079063001potentially active as:antitumor agentsmonoacylglycerol lipase inhibitorsantibacterial drugsfusarium oxysporum agentsY.-X. WuK. PengJ.-H. LiZ.-B. Dong*Wuhan Institute of Technology,P. R. of ChinaHubei University,P. R. of ChinaPaperbifunctional C5 dienes (key building blocks)Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloadditionfor Diversity-Oriented Synthesis of Structurally coumarin] HybridsX.-W. LiuS.-Q. ChangQ.-L. WangS. ChenJ.-X. WangW. ZhouY. Zhou*R3R3HNCO2HR2O NRROOHNDABCO (1.5 equiv)4OODCM, rt, 8 hR2ON1R1R430 examplesGuizhou University of TraditionalChinese Medicine,P. R. of Chinaup to 90% yield and 15:1 drNH2 HClOR2ONR1 R3Decarboxylative mediated 1,3-dipolar cycloadditionRegioselective, exo'-selective and diversity-oriented synthesisOur goal: a hybrid of three pharmacores for drug discoveryThe first example of cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarinsPaper3018This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Synthesis
IXSynthesis 2020, 52, 3029–3035DOI: 10.1055/s-0040-1707193J. SynofzikO. BakulinaO. BalabasD. Dar’inM. Krasavin*Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonylazetidin2-ones via Microwave-Assisted Tandem Wolff Rearrangement–Staudinger CycloadditionO O OSR1R3R2N2NR4O O R2SR1toluene, MW150 C, 1 hSynthesisR. H. V. NishimuraN. WeidmannP. Knochel*OPreparation of Diorganomagnesium Reagents by Halogen–LithiumExchange of Functionalized Heteroaryl Halides and Subsequent in situTrapping with MgCl2·LiCl in Continuous FlowFlowFMgF HO2NFENFadamantanone1.5 equiv25 C, 10 min1.0 equiv MgCl2·LiCl0.5 equivSynthesis 2020, 52, 3047–3057DOI: 10.1055/s-0040-1707340H.-J. ZhouW. ZhouX.-L. Liu*Y.-P. TianJ.-X. WangY. Zhou*Guizhou University of TraditionalChinese Medicine,P. R. of China3036Batch12 mL min–1FBrSynthesisPaper0.1 s–78 CnBuLi1.5 equivLudwig-Maximilians-UniversitätMünchen, Germany3029NR4R321 examples22–81%dr 1.6:1 to 20:1Saint Petersburg State University, Russian FederationSynthesis 2020, 52, 3036–3046DOI: 10.1055/s-0040-1707167PaperN95%FCatalytic Asymmetric Domino Michael/Annulation Reaction of Bifunctional Chromone Synthons with , -Unsaturated -Keto Esters: RapidAccess to Polysubstituted Spirocyclic HexahydroxanthonesR2R2OOδOOArNBocC4 synthonsC1 (20 mol%), Et2O, rt, 5 dR1ONBocup to 76% yield, 99% ee and 20:1 dr23 examplesthe first example of enone as C2 synthon in chemistry of chromonespotential biologically active moleculesCF3SOδ–OOEtOOEtArOR1O NNHNHC1CF3Paper3047This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Synthesis
XSynthesis 2020, 52, 3058–3064DOI: 10.1055/s-0040-1707204B. WangQ. ZhangZ. GuoK. Ablajan*Iodine- and TBHP-Promoted Acylation of Benzothiazoles underMetal-Free ConditionsONR1 SSynthesisArSmetal-freebroad scopelower temperature20 examples78–94% yieldsMetal-Free Insertion of Sulfoxonium Ylides into Arylamines in WaterSynthesis 2020, 52, 3065–3070DOI: 10.1055/s-0040-1707186H. HeK. YanJ. LiR. LaiY. LuoM. Guan*Y. Wu*R1DMSO60 CXinjiang University,P. R. of China3058ONI2, TBHPArPaperOOSR1R3H NR4R2NR1H2O3065R3OH PaperR4R2 Metal-free Water as solvent Up to 87% yield 25 examples Suitable for late-stage modificationSichuan University, P. R. of ChinaSynthesisSynthesis 2020, 52, 3071–3076DOI: 10.1055/s-0040-1707158Synthesis of Benzo-Fused 11H-Pyrido[2,1-b]quinazolin-11-ones by aBuchwald–Hartwig Coupling/Pyridine Dearomatization Sequence inEucalyptolJ. F. CamposA. Pacheco-BenichouC. FruitT. BessonS. Berteina-Raboin*NH2HetOPd(OAc)2 (3 mol%)Xantphos (4 mol%)Cs2CO3 (2.5 equiv.)Br RNSSNH2ONOONNNH2ON NHOStarting anthranilic acid OOONClNNH2ORBrBrBrONeucalyptol120 C, 18–24 hONH2N3071NHetOUniversité d’Orléans UMR-CNRS7311, FrancePaperORNN NHOPyridoquinazolinone derivativesRThis document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Synthesis
XISynthesis 2020, 52, 3077–3085DOI: 10.1055/s-0040-1707184F. EmmetiereA. J. Grenning*University of Florida, USAFunctional Group Interconversion of Alkylidenemalononitriles toPrimary Alcohols by a Cooperative Redox OperationNCR1NaBH4 and O2 (1 atm)alternating redox operationsCNRSynthesisSynthesis 2020, 52, 3086–3094DOI: 10.1055/s-0040-1707347M. TryniszewskiR. BujokR. GańczarczykZ. Wróbel*Polish Academy of Sciences,PolandR1via1RThree Metal-Free Steps in One Operation in One PotOHC O2HNX1YX2PBu3X2ZNX1140–180 C, 48 hZNYR27–83% yieldY CH CH, N CH, SZ CH, NSynthesisR22Reductive Condensation of a Nitro Group with Carboxylic AcidsPromoted by Phosphorus(III) Compounds: A Short Route to5H-Dibenzo[b,e][1,4]diazepin-11(10H)-onesN O2 R3077OHONCR2PaperX Cl, OMe, CF3, CN, Ph, MeR H, AlkylPaper3086This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Synthesis
Date, Signature tc2020ss.fm 10/1/20 Reviews and Full Papers in Chemical Synthesis 2020 Vol. 52, No. 20 Synthesis October II Synthesis Synthesis Synthesis 2020, 52, 2899-2921 DOI: 10.1055/s-0040-1707136 C.-M. Chan Y.-C. Chow W.-Y. Yu* The Hong Kong Polytechnic Uni-versity, Hong Kong Recent Advances in Photocatalytic C-N Bond Coupling .
