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Volumn 3, Issue 1, 2017, Pages 31-55

Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks

Author keywords

boron; catalysis; reactivity; selectivity; synthesis

Indexed keywords


EID: 85023165739     PISSN: 24519308     EISSN: 24519294     Source Type: Journal    
DOI: 10.1016/j.chempr.2017.05.008     Document Type: Review
Times cited : (435)

References (109)
  • 1
    • 84958641974 scopus 로고    scopus 로고
    • Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine
    • Wiley-VCH
    • Hall, D.G., Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. 2005, Wiley-VCH.
    • (2005)
    • Hall, D.G.1
  • 2
    • 0037112673 scopus 로고    scopus 로고
    • Palladium-catalyzed coupling reactions of aryl chlorides
    • Littke, A.F., Fu, G.C., Palladium-catalyzed coupling reactions of aryl chlorides. Angew. Chem. Int. Ed. 41 (2002), 4176–4211.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4176-4211
    • Littke, A.F.1    Fu, G.C.2
  • 3
    • 49249152617 scopus 로고
    • A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides
    • Miyaura, N., Yamada, K., Suzuki, A., A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett. 36 (1979), 3437–3440.
    • (1979) Tetrahedron Lett. , vol.36 , pp. 3437-3440
    • Miyaura, N.1    Yamada, K.2    Suzuki, A.3
  • 4
    • 84889001492 scopus 로고    scopus 로고
    • Selection of boron reagents for Suzuki–Miyaura coupling
    • For a review, see
    • For a review, seeLennox, A.J.J., Lloyd-Jones, G.C., Selection of boron reagents for Suzuki–Miyaura coupling. Chem. Soc. Rev. 43 (2014), 412–443.
    • (2014) Chem. Soc. Rev. , vol.43 , pp. 412-443
    • Lennox, A.J.J.1    Lloyd-Jones, G.C.2
  • 5
    • 3142514770 scopus 로고
    • Palladium(0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: a direct procedure for arylboronic esters
    • Ishiyama, T., Murata, M., Miyaura, M., Palladium(0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: a direct procedure for arylboronic esters. J. Org. Chem. 60 (1995), 7508–7510.
    • (1995) J. Org. Chem. , vol.60 , pp. 7508-7510
    • Ishiyama, T.1    Murata, M.2    Miyaura, M.3
  • 6
    • 0001307257 scopus 로고
    • Organoboranes. 31. A simple preparation of boronic esters from organolithium reagents and selected trialkoxyboranes
    • Brown, H.C., Cole, T.E., Organoboranes. 31. A simple preparation of boronic esters from organolithium reagents and selected trialkoxyboranes. Organometallics 2 (1983), 1316–1319.
    • (1983) Organometallics , vol.2 , pp. 1316-1319
    • Brown, H.C.1    Cole, T.E.2
  • 7
    • 84880531972 scopus 로고    scopus 로고
    • A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates
    • For a review, see
    • For a review, seeChow, W.K., Yuen, O.Y., Choy, P.Y., So, C.M., Lau, C.P., Wong, W.T., Kwong, F.Y., A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates. RSC Adv. 3 (2013), 12518–12539.
    • (2013) RSC Adv. , vol.3 , pp. 12518-12539
    • Chow, W.K.1    Yuen, O.Y.2    Choy, P.Y.3    So, C.M.4    Lau, C.P.5    Wong, W.T.6    Kwong, F.Y.7
  • 8
    • 84864338659 scopus 로고    scopus 로고
    • Transition-metal-catalyzed borylation of organic halides with hydroboranes
    • For a review, see
    • For a review, seeMurata, M., Transition-metal-catalyzed borylation of organic halides with hydroboranes. Heterocycles 85 (2012), 1795–1819.
    • (2012) Heterocycles , vol.85 , pp. 1795-1819
    • Murata, M.1
  • 9
    • 84930680277 scopus 로고    scopus 로고
    • Ipso-borylation of aryl ethers via Ni-catalyzed C−OMe cleavage
    • Zarate, C., Manzano, R., Martin, R., Ipso-borylation of aryl ethers via Ni-catalyzed C−OMe cleavage. J. Am. Chem. Soc. 137 (2015), 6754–6757.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 6754-6757
    • Zarate, C.1    Manzano, R.2    Martin, R.3
  • 10
    • 84947810665 scopus 로고    scopus 로고
    • Ni/Cu-catalyzed defluoroborylation of fluoroarenes for diverse C−F bond functionalizations
    • Niwa, T., Ochiai, H., Watanabe, Y., Hosoya, T., Ni/Cu-catalyzed defluoroborylation of fluoroarenes for diverse C−F bond functionalizations. J. Am. Chem. Soc. 137 (2015), 14313–14318.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 14313-14318
    • Niwa, T.1    Ochiai, H.2    Watanabe, Y.3    Hosoya, T.4
  • 11
    • 0033603859 scopus 로고    scopus 로고
    • Stoichiometric and catalytic B-C bond formation from unactivated hydrocarbons and boranes
    • Iverson, C.N., Smith, M.R. III, Stoichiometric and catalytic B-C bond formation from unactivated hydrocarbons and boranes. J. Am. Chem. Soc. 121 (1999), 7696–7697.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7696-7697
    • Iverson, C.N.1    Smith, M.R.2
  • 12
    • 0037160365 scopus 로고    scopus 로고
    • Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
    • Ishiyama, T., Takagi, J., Ishida, K., Miyaura, N., Anastasi, N.R., Hartwig, J.F., Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate. J. Am. Chem. Soc. 124 (2002), 390–391.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 390-391
    • Ishiyama, T.1    Takagi, J.2    Ishida, K.3    Miyaura, N.4    Anastasi, N.R.5    Hartwig, J.F.6
  • 13
    • 0000644870 scopus 로고    scopus 로고
    • Formation of aryl- and benzylboronate esters by rhodium-catalyzed C−H bond functionalization with pinacolborane
    • Shimada, S., Batsanov, A.S., Howard, J.A.K., Marder, T.B., Formation of aryl- and benzylboronate esters by rhodium-catalyzed C−H bond functionalization with pinacolborane. Angew. Chem. Int. Ed. 40 (2001), 2168–2171.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2168-2171
    • Shimada, S.1    Batsanov, A.S.2    Howard, J.A.K.3    Marder, T.B.4
  • 15
    • 84862908407 scopus 로고    scopus 로고
    • Pd-catalyzed oxidative ortho-C–H borylation of arenes
    • Dai, H.-X., Yu, J.-Q., Pd-catalyzed oxidative ortho-C–H borylation of arenes. J. Am. Chem. Soc. 134 (2012), 134–137.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 134-137
    • Dai, H.-X.1    Yu, J.-Q.2
  • 16
    • 84896510240 scopus 로고    scopus 로고
    • Iridium-catalyzed C–H borylation of heteroarenes: scope, regioselectivity, application to late-stage functionalization, and mechanism
    • Larsen, M.A., Hartwig, J.F., Iridium-catalyzed C–H borylation of heteroarenes: scope, regioselectivity, application to late-stage functionalization, and mechanism. J. Am. Chem. Soc. 136 (2014), 4287–4299.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 4287-4299
    • Larsen, M.A.1    Hartwig, J.F.2
  • 17
    • 84870896468 scopus 로고    scopus 로고
    • Anomalous reactivity of silylborane: transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems
    • Yamamoto, E., Izumi, K., Horita, Y., Ito, H., Anomalous reactivity of silylborane: transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems. J. Am. Chem. Soc. 134 (2012), 19997–20000.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 19997-20000
    • Yamamoto, E.1    Izumi, K.2    Horita, Y.3    Ito, H.4
  • 18
    • 0034295260 scopus 로고    scopus 로고
    • Convenient preparation of silylboranes
    • Suginome, M., Matsuda, T., Ito, Y., Convenient preparation of silylboranes. Organometallics 19 (2000), 4647–4649.
    • (2000) Organometallics , vol.19 , pp. 4647-4649
    • Suginome, M.1    Matsuda, T.2    Ito, Y.3
  • 19
    • 84971291373 scopus 로고    scopus 로고
    • Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
    • Chen, K., Zhang, S., He, P., Li, P., Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions. Chem. Sci. 7 (2016), 3676–3680.
    • (2016) Chem. Sci. , vol.7 , pp. 3676-3680
    • Chen, K.1    Zhang, S.2    He, P.3    Li, P.4
  • 20
    • 84960380643 scopus 로고    scopus 로고
    • Scalable, metal- and additive-free, photoinduced borylation of haloarenes and quaternary arylammonium salts
    • Mfuh, A.M., Doyle, J.D., Chhetri, B., Arman, H.D., Larionov, O.V., Scalable, metal- and additive-free, photoinduced borylation of haloarenes and quaternary arylammonium salts. J. Am. Chem. Soc. 138 (2016), 2985–2988.
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 2985-2988
    • Mfuh, A.M.1    Doyle, J.D.2    Chhetri, B.3    Arman, H.D.4    Larionov, O.V.5
  • 21
    • 84940557692 scopus 로고    scopus 로고
    • Metal-free catalytic C-H bond activation and borylation of heteroarenes
    • Legare, M.-A., Courtemanche, M.-A., Rochette, E., Fontaine, F.-G., Metal-free catalytic C-H bond activation and borylation of heteroarenes. Science 349 (2015), 513–516.
    • (2015) Science , vol.349 , pp. 513-516
    • Legare, M.-A.1    Courtemanche, M.-A.2    Rochette, E.3    Fontaine, F.-G.4
  • 23
    • 84959377917 scopus 로고    scopus 로고
    • Catalyst-free synthesis of borylated lactones from esters via electrophilic oxyboration
    • Faizi, D.J., Issaian, A., Davis, A.J., Blum, S.A., Catalyst-free synthesis of borylated lactones from esters via electrophilic oxyboration. J. Am. Chem. Soc. 138 (2016), 2126–2129.
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 2126-2129
    • Faizi, D.J.1    Issaian, A.2    Davis, A.J.3    Blum, S.A.4
  • 24
    • 84991338039 scopus 로고    scopus 로고
    • Catalyst-free formal thioboration to synthesize borylated benzothiophenes and dihydrothiophenes
    • Faizi, D.J., Davis, A.J., Meany, F.B., Blum, S.A., Catalyst-free formal thioboration to synthesize borylated benzothiophenes and dihydrothiophenes. Angew. Chem. Int. Ed. 55 (2016), 14286–14290.
    • (2016) Angew. Chem. Int. Ed. , vol.55 , pp. 14286-14290
    • Faizi, D.J.1    Davis, A.J.2    Meany, F.B.3    Blum, S.A.4
  • 26
    • 84898878174 scopus 로고    scopus 로고
    • Air- and moisture-stable amphoteric molecules: enabling reagents in synthesis
    • For a review, see
    • For a review, seeHe, Z., Zajdlik, A., Yudin, A.K., Air- and moisture-stable amphoteric molecules: enabling reagents in synthesis. Acc. Chem. Res. 47 (2014), 1029–1040.
    • (2014) Acc. Chem. Res. , vol.47 , pp. 1029-1040
    • He, Z.1    Zajdlik, A.2    Yudin, A.K.3
  • 27
    • 0002594370 scopus 로고
    • New bicyclic organylboronic esters derived from iminodiacetic acids
    • Mancilla, T., Contreras, R., New bicyclic organylboronic esters derived from iminodiacetic acids. J. Organomet. Chem. 307 (1986), 1–6.
    • (1986) J. Organomet. Chem. , vol.307 , pp. 1-6
    • Mancilla, T.1    Contreras, R.2
  • 28
    • 54849403713 scopus 로고    scopus 로고
    • Multistep synthesis of complex boronic acids from simple MIDA boronates
    • Gillis, E.P., Burke, M.D., Multistep synthesis of complex boronic acids from simple MIDA boronates. J. Am. Chem. Soc. 130 (2008), 14084–14085.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14084-14085
    • Gillis, E.P.1    Burke, M.D.2
  • 30
    • 84937731639 scopus 로고    scopus 로고
    • Synthesis of previously inaccessible borylated heterocycle motifs using novel boron-containing amphoteric molecules
    • Trinchera, P., Corless, V.B., Yudin, A.K., Synthesis of previously inaccessible borylated heterocycle motifs using novel boron-containing amphoteric molecules. Angew. Chem. Int. Ed. 54 (2015), 9038–9041.
    • (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 9038-9041
    • Trinchera, P.1    Corless, V.B.2    Yudin, A.K.3
  • 31
    • 71049126548 scopus 로고    scopus 로고
    • Escape from flatland: increasing saturation as an approach to improving clinical success
    • Lovering, F., Bikker, J., Humblet, C., Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52 (2009), 6752–6756.
    • (2009) J. Med. Chem. , vol.52 , pp. 6752-6756
    • Lovering, F.1    Bikker, J.2    Humblet, C.3
  • 36
    • 0013428265 scopus 로고
    • Hydroboration—a powerful synthetic tool
    • Brown, H.C., Hydroboration—a powerful synthetic tool. Tetrahedron 12 (1961), 117–138.
    • (1961) Tetrahedron , vol.12 , pp. 117-138
    • Brown, H.C.1
  • 37
    • 84901710845 scopus 로고    scopus 로고
    • Arylboration of alkenes by cooperative palladium/copper catalysis
    • Semba, K., Nakao, Y., Arylboration of alkenes by cooperative palladium/copper catalysis. J. Am. Chem. Soc. 136 (2014), 7567–7570.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 7567-7570
    • Semba, K.1    Nakao, Y.2
  • 38
    • 84908372936 scopus 로고    scopus 로고
    • Alkene carboboration enabled by synergistic catalysis
    • Smith, K.B., Logan, K.M., You, W., Brown, M.K., Alkene carboboration enabled by synergistic catalysis. Chem. Eur. J. 20 (2014), 12032–12036.
    • (2014) Chem. Eur. J. , vol.20 , pp. 12032-12036
    • Smith, K.B.1    Logan, K.M.2    You, W.3    Brown, M.K.4
  • 39
    • 84927748609 scopus 로고    scopus 로고
    • Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes
    • Logan, K.M., Smith, K.B., Brown, M.K., Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes. Angew. Chem. Int. Ed. 54 (2015), 5228–5231.
    • (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 5228-5231
    • Logan, K.M.1    Smith, K.B.2    Brown, M.K.3
  • 40
    • 84952896677 scopus 로고    scopus 로고
    • A Cu/Pd cooperative catalysis for enantioselective allylboration of alkenes
    • Jia, T., Cao, P., Wang, B., Lou, Y., Yin, X., Wang, M., Liao, J., A Cu/Pd cooperative catalysis for enantioselective allylboration of alkenes. J. Am. Chem. Soc. 137 (2015), 13760–13763.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 13760-13763
    • Jia, T.1    Cao, P.2    Wang, B.3    Lou, Y.4    Yin, X.5    Wang, M.6    Liao, J.7
  • 41
    • 85008937483 scopus 로고    scopus 로고
    • Catalytic enantioselective arylboration of alkenylarenes
    • Logan, K.M., Brown, M.K., Catalytic enantioselective arylboration of alkenylarenes. Angew. Chem. Int. Ed. 56 (2017), 851–855.
    • (2017) Angew. Chem. Int. Ed. , vol.56 , pp. 851-855
    • Logan, K.M.1    Brown, M.K.2
  • 42
    • 84862079156 scopus 로고    scopus 로고
    • Metal-free catalytic enantioselective C−B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes
    • Wu, H., Radomkit, S., O'Brien, J.M., Hoveyda, A.H., Metal-free catalytic enantioselective C−B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes. J. Am. Chem. Soc. 134 (2012), 8277–8285.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 8277-8285
    • Wu, H.1    Radomkit, S.2    O'Brien, J.M.3    Hoveyda, A.H.4
  • 43
    • 84896476338 scopus 로고    scopus 로고
    • Enantioselective synthesis of boron-substituted quaternary carbonstereogenic centers through NHC-catalyzed conjugate additions of(pinacolato)boron units to enones
    • Radomkit, S., Hoveyda, A.H., Enantioselective synthesis of boron-substituted quaternary carbonstereogenic centers through NHC-catalyzed conjugate additions of(pinacolato)boron units to enones. Angew. Chem. Int. Ed. 53 (2014), 3387–3391.
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 3387-3391
    • Radomkit, S.1    Hoveyda, A.H.2
  • 44
    • 84987784627 scopus 로고    scopus 로고
    • Accessing both retention and inversion pathways in stereospecific, nickel-catalyzed Miyaura borylations of allylic pivalates
    • Zhou, Q., Srinivas, H.D., Zhang, S., Watson, M.P., Accessing both retention and inversion pathways in stereospecific, nickel-catalyzed Miyaura borylations of allylic pivalates. J. Am. Chem. Soc. 138 (2016), 11989–11995.
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 11989-11995
    • Zhou, Q.1    Srinivas, H.D.2    Zhang, S.3    Watson, M.P.4
  • 45
    • 84969535016 scopus 로고    scopus 로고
    • Big data from pharmaceutical patents: a computational analysis of medicinal chemists’ bread and butter
    • Nadine Schneider, N., Lowe, D.M., Sayle, R.A., Tarselli, M.A., Landrum, G.A., Big data from pharmaceutical patents: a computational analysis of medicinal chemists’ bread and butter. J. Med. Chem. 59 (2016), 4385–4402.
    • (2016) J. Med. Chem. , vol.59 , pp. 4385-4402
    • Nadine Schneider, N.1    Lowe, D.M.2    Sayle, R.A.3    Tarselli, M.A.4    Landrum, G.A.5
  • 46
    • 84969617464 scopus 로고    scopus 로고
    • Analysis of past and present synthetic methodologies on medicinal chemistry: where have all the new reactions gone?
    • Brown, D.G., Boström, J., Analysis of past and present synthetic methodologies on medicinal chemistry: where have all the new reactions gone?. J. Med. Chem. 59 (2016), 4443–4458.
    • (2016) J. Med. Chem. , vol.59 , pp. 4443-4458
    • Brown, D.G.1    Boström, J.2
  • 47
    • 57549099215 scopus 로고    scopus 로고
    • Palladium-catalyzed Suzuki−Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands
    • For a review, see
    • For a review, seeMartin, R., Buchwald, S.L., Palladium-catalyzed Suzuki−Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. Acc. Chem. Res. 41 (2008), 1461–1473.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1461-1473
    • Martin, R.1    Buchwald, S.L.2
  • 48
    • 84948784009 scopus 로고    scopus 로고
    • Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules
    • For a review, see
    • For a review, seeXu, L., Zhang, S., Li, P., Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules. Chem. Soc. Rev. 44 (2015), 8848–8858.
    • (2015) Chem. Soc. Rev. , vol.44 , pp. 8848-8858
    • Xu, L.1    Zhang, S.2    Li, P.3
  • 49
    • 84939547705 scopus 로고    scopus 로고
    • From synthesis to function via iterative assembly of N-methyliminodiacetic acid boronate building blocks
    • For a review, see
    • For a review, seeLi, J., Grillo, A.S., Burke, M.D., From synthesis to function via iterative assembly of N-methyliminodiacetic acid boronate building blocks. Acc. Chem. Res. 48 (2015), 2297–2307.
    • (2015) Acc. Chem. Res. , vol.48 , pp. 2297-2307
    • Li, J.1    Grillo, A.S.2    Burke, M.D.3
  • 50
    • 33846588529 scopus 로고    scopus 로고
    • Boron-masking strategy for the selective synthesis of oligoarenes via iterative Suzuki–Miyaura coupling
    • For the first report of this protecting group, see
    • For the first report of this protecting group, seeNoguchi, H., Hojo, K., Suginome, M., Boron-masking strategy for the selective synthesis of oligoarenes via iterative Suzuki–Miyaura coupling. J. Am. Chem. Soc. 129 (2007), 758–759.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 758-759
    • Noguchi, H.1    Hojo, K.2    Suginome, M.3
  • 51
    • 0013844446 scopus 로고
    • Automated synthesis of peptides
    • Merrifield, R.B., Automated synthesis of peptides. Science 150 (1965), 178–185.
    • (1965) Science , vol.150 , pp. 178-185
    • Merrifield, R.B.1
  • 53
    • 34249828956 scopus 로고    scopus 로고
    • A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks
    • Gillis, E.P., Burke, M.D., A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks. J. Am. Chem. Soc. 129 (2007), 6716–6717.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6716-6717
    • Gillis, E.P.1    Burke, M.D.2
  • 54
    • 84911460873 scopus 로고    scopus 로고
    • Chemoselective boronic ester synthesis by controlled speciation
    • Fyfe, J.W.B., Seath, C.P., Watson, A.J.B., Chemoselective boronic ester synthesis by controlled speciation. Angew. Chem. Int. Ed. 53 (2014), 12077–12080.
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 12077-12080
    • Fyfe, J.W.B.1    Seath, C.P.2    Watson, A.J.B.3
  • 57
    • 84939000648 scopus 로고    scopus 로고
    • Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control
    • Seath, C.P., Fyfe, J.W.B., Molloy, J.J., Watson, A.J.B., Tandem chemoselective Suzuki-Miyaura cross-coupling enabled by nucleophile speciation control. Angew. Chem. Int. Ed. 54 (2015), 9976–9979.
    • (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 9976-9979
    • Seath, C.P.1    Fyfe, J.W.B.2    Molloy, J.J.3    Watson, A.J.B.4
  • 58
    • 0034600318 scopus 로고    scopus 로고
    • Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions
    • Littke, A.F., Dai, C., Fu, G.C., Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions. J. Am. Chem. Soc. 122 (2000), 4020–4028.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4020-4028
    • Littke, A.F.1    Dai, C.2    Fu, G.C.3
  • 59
    • 67749113467 scopus 로고    scopus 로고
    • Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration
    • Imao, D., Glasspoole, B.W., Laberge, V.S., Crudden, C.M., Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration. J. Am. Chem. Soc. 131 (2009), 5024–5025.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5024-5025
    • Imao, D.1    Glasspoole, B.W.2    Laberge, V.S.3    Crudden, C.M.4
  • 61
    • 84878638599 scopus 로고    scopus 로고
    • Transition-metal-catalyzed Suzuki–Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts
    • For a review, see
    • For a review, seeHan, F.-S., Transition-metal-catalyzed Suzuki–Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts. Chem. Soc. Rev. 42 (2013), 5270–5298.
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 5270-5298
    • Han, F.-S.1
  • 62
    • 84928905637 scopus 로고    scopus 로고
    • A modular, air-stable nickel precatalyst
    • Shields, J.D., Gray, E.E., Doyle, A.G., A modular, air-stable nickel precatalyst. Org. Lett. 17 (2015), 2166–2169.
    • (2015) Org. Lett. , vol.17 , pp. 2166-2169
    • Shields, J.D.1    Gray, E.E.2    Doyle, A.G.3
  • 63
    • 84924657158 scopus 로고    scopus 로고
    • Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups
    • Li, X., Zou, G., Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups. Chem. Commun. 51 (2015), 5089–5092.
    • (2015) Chem. Commun. , vol.51 , pp. 5089-5092
    • Li, X.1    Zou, G.2
  • 64
    • 84951209108 scopus 로고    scopus 로고
    • Nickel-catalysed Suzuki–Miyaura coupling of amides
    • Weires, N.A., Baker, E.L., Garg, N.K., Nickel-catalysed Suzuki–Miyaura coupling of amides. Nat. Chem. 8 (2016), 75–79.
    • (2016) Nat. Chem. , vol.8 , pp. 75-79
    • Weires, N.A.1    Baker, E.L.2    Garg, N.K.3
  • 65
    • 84941003135 scopus 로고    scopus 로고
    • Sterically-controlled Pd-catalyzed chemoselective ketone synthesis via N–C cleavage in twisted amides
    • Meng, G., Szostak, M., Sterically-controlled Pd-catalyzed chemoselective ketone synthesis via N–C cleavage in twisted amides. Org. Lett. 17 (2015), 4364–4367.
    • (2015) Org. Lett. , vol.17 , pp. 4364-4367
    • Meng, G.1    Szostak, M.2
  • 66
    • 84973097170 scopus 로고    scopus 로고
    • Synthesis of biaryls via nickel catalyzed Suzuki–Miyaura coupling of amides by carbon–nitrogen cleavage
    • Shi, S., Meng, G., Szostak, M., Synthesis of biaryls via nickel catalyzed Suzuki–Miyaura coupling of amides by carbon–nitrogen cleavage. Angew. Chem. Int. Ed. 55 (2016), 6959–6963.
    • (2016) Angew. Chem. Int. Ed. , vol.55 , pp. 6959-6963
    • Shi, S.1    Meng, G.2    Szostak, M.3
  • 67
    • 67649488045 scopus 로고    scopus 로고
    • Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality
    • For a review, see
    • For a review, seeChen, X., Engle, K.M., Wang, D.-H., Yu, J.-Q., Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew. Chem. Int. Ed. 48 (2009), 5094–5115.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115
    • Chen, X.1    Engle, K.M.2    Wang, D.-H.3    Yu, J.-Q.4
  • 68
    • 85027922490 scopus 로고    scopus 로고
    • Ruthenium(II)-catalyzed C-H arylation of anilides with boronic acids, borinic acids and potassium trifluoroborates
    • Hubrich, J., Himmler, T., Rodefeld, L., Ackermann, L., Ruthenium(II)-catalyzed C-H arylation of anilides with boronic acids, borinic acids and potassium trifluoroborates. Adv. Synth. Catal. 357 (2015), 474–480.
    • (2015) Adv. Synth. Catal. , vol.357 , pp. 474-480
    • Hubrich, J.1    Himmler, T.2    Rodefeld, L.3    Ackermann, L.4
  • 69
    • 84977104053 scopus 로고    scopus 로고
    • Ruthenium(II)-catalyzed regioselective C−H arylation of cyclic and N,N-dialkyl benzamides with boronic acids by weak coordination
    • Nareddy, P., Jordan, F., Brenner-Moyer, S.E., Szostak, M., Ruthenium(II)-catalyzed regioselective C−H arylation of cyclic and N,N-dialkyl benzamides with boronic acids by weak coordination. ACS Catal. 6 (2016), 4755–4759.
    • (2016) ACS Catal. , vol.6 , pp. 4755-4759
    • Nareddy, P.1    Jordan, F.2    Brenner-Moyer, S.E.3    Szostak, M.4
  • 71
    • 84881052216 scopus 로고    scopus 로고
    • Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes
    • Coombs, J.R., Haeffner, F., Kliman, L.T., Morken, J.P., Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes. J. Am. Chem. Soc. 135 (2013), 11222–11231.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 11222-11231
    • Coombs, J.R.1    Haeffner, F.2    Kliman, L.T.3    Morken, J.P.4
  • 72
    • 84892589818 scopus 로고    scopus 로고
    • Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling
    • Mlynarski, S.N., Schuster, C.H., Morken, J.P., Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling. Nature 505 (2014), 386–390.
    • (2014) Nature , vol.505 , pp. 386-390
    • Mlynarski, S.N.1    Schuster, C.H.2    Morken, J.P.3
  • 73
    • 84885466170 scopus 로고    scopus 로고
    • Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: enantioselective synthesis of optically active 1,2-diols
    • Toribatake, K., Nishiyama, H., Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: enantioselective synthesis of optically active 1,2-diols. Angew. Chem. Int. Ed. 52 (2013), 11011–11015.
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 11011-11015
    • Toribatake, K.1    Nishiyama, H.2
  • 74
    • 77955574719 scopus 로고    scopus 로고
    • 3-carbon in 1,1-diborylalkanes at room temperature
    • For the first example of neighboring-group activation in cross-coupling, see
    • 3-carbon in 1,1-diborylalkanes at room temperature. J. Am. Chem. Soc. 132 (2010), 11033–11035.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11033-11035
    • Endo, K.1    Ohkubo, T.2    Hirokami, M.3    Shibata, T.4
  • 75
    • 84937139885 scopus 로고    scopus 로고
    • Hydroxyl-directed cross-coupling: a scalable synthesis of debromohamigeran E and other targets of interest
    • Blaisdell, T.P., Morken, J.P., Hydroxyl-directed cross-coupling: a scalable synthesis of debromohamigeran E and other targets of interest. J. Am. Chem. Soc. 137 (2015), 8712–8715.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 8712-8715
    • Blaisdell, T.P.1    Morken, J.P.2
  • 78
    • 70349782336 scopus 로고    scopus 로고
    • Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions
    • For a review of the use of secondary alkyl halides in cross-coupling, see
    • For a review of the use of secondary alkyl halides in cross-coupling, seeRudolph, A., Lautens, M., Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions. Angew. Chem. Int. Ed. 48 (2009), 2656–2670.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2656-2670
    • Rudolph, A.1    Lautens, M.2
  • 80
    • 84939857631 scopus 로고    scopus 로고
    • Organotrifluoroborates: another branch of the mighty oak
    • For a review on organotrifluoroborates, see
    • For a review on organotrifluoroborates, seeMolander, G.A., Organotrifluoroborates: another branch of the mighty oak. J. Org. Chem. 80 (2015), 7837–7848.
    • (2015) J. Org. Chem. , vol.80 , pp. 7837-7848
    • Molander, G.A.1
  • 81
    • 84904800842 scopus 로고    scopus 로고
    • Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
    • Tellis, J.C., Primer, D.N., Molander, G.A., Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis. Science 345 (2014), 433–436.
    • (2014) Science , vol.345 , pp. 433-436
    • Tellis, J.C.1    Primer, D.N.2    Molander, G.A.3
  • 83
    • 84942885483 scopus 로고    scopus 로고
    • Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis
    • Yamashita, Y., Tellis, J.C., Molander, G.A., Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis. Proc. Natl. Acad. Sci. USA 112 (2015), 12026–12029.
    • (2015) Proc. Natl. Acad. Sci. USA , vol.112 , pp. 12026-12029
    • Yamashita, Y.1    Tellis, J.C.2    Molander, G.A.3
  • 85
    • 80054972215 scopus 로고    scopus 로고
    • 3)–H bonds
    • For a review, see
    • 3)–H bonds. Chem. Soc. Rev. 40 (2011), 4902–4911.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 4902-4911
    • Baudoin, O.1
  • 87
    • 84955390840 scopus 로고    scopus 로고
    • Ligand-enabled catalytic C-H arylation of aliphatic amines by a four-membered-ring cyclopalladation pathway
    • He, C., Gaunt, M.J., Ligand-enabled catalytic C-H arylation of aliphatic amines by a four-membered-ring cyclopalladation pathway. Angew. Chem. Int. Ed. 54 (2015), 15840–15844.
    • (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 15840-15844
    • He, C.1    Gaunt, M.J.2
  • 88
    • 85015238847 scopus 로고    scopus 로고
    • Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides
    • Jain, P., Verma, P., Xia, G., Yu, J.-Q., Enantioselective amine α-functionalization via palladium-catalysed C–H arylation of thioamides. Nat. Chem. 9 (2017), 140–144.
    • (2017) Nat. Chem. , vol.9 , pp. 140-144
    • Jain, P.1    Verma, P.2    Xia, G.3    Yu, J.-Q.4
  • 90
    • 0000122303 scopus 로고
    • α-Chloro boronic esters from homologation of boronic esters
    • Matteson, D.S., Majumdar, D., α-Chloro boronic esters from homologation of boronic esters. J. Am. Chem. Soc. 102 (1980), 7588–7590.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 7588-7590
    • Matteson, D.S.1    Majumdar, D.2
  • 91
    • 84926433821 scopus 로고    scopus 로고
    • Toward ideality: the synthesis of (+)-kalkitoxin and (+)-hydroxyphthioceranic acid by assembly-line synthesis
    • Balieu, S., Hallett, G.E., Burns, M., Bootwicha, T., Studley, J., Aggarwal, V.K., Toward ideality: the synthesis of (+)-kalkitoxin and (+)-hydroxyphthioceranic acid by assembly-line synthesis. J. Am. Chem. Soc. 137 (2015), 4398–4403.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 4398-4403
    • Balieu, S.1    Hallett, G.E.2    Burns, M.3    Bootwicha, T.4    Studley, J.5    Aggarwal, V.K.6
  • 92
    • 0042066532 scopus 로고    scopus 로고
    • Total synthesis of (+)-kalkitoxin
    • White, J.D., Lee, C.-S., Xu, Q., Total synthesis of (+)-kalkitoxin. Chem. Commun., 2003, 2012–2013.
    • (2003) Chem. Commun. , pp. 2012-2013
    • White, J.D.1    Lee, C.-S.2    Xu, Q.3
  • 93
    • 84900322702 scopus 로고    scopus 로고
    • A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates
    • Sun, C., Potter, B., Morken, J.P., A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates. J. Am. Chem. Soc. 136 (2014), 6534–6537.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 6534-6537
    • Sun, C.1    Potter, B.2    Morken, J.P.3
  • 94
    • 84930222017 scopus 로고    scopus 로고
    • Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through cu-catalyzed additions of alkylboronates to aldehydes
    • Joannou, M.V., Moyer, B.S., Meek, S.J., Enantio- and diastereoselective synthesis of 1,2-hydroxyboronates through cu-catalyzed additions of alkylboronates to aldehydes. J. Am. Chem. Soc. 137 (2015), 6176–6179.
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 6176-6179
    • Joannou, M.V.1    Moyer, B.S.2    Meek, S.J.3
  • 95
    • 84954455972 scopus 로고    scopus 로고
    • Silver(I)-catalyzed diastereoselective synthesis of anti-1,2-hydroxyboronates
    • Joannou, M.V., Moyer, B.S., Goldfogel, M.J., Meek, S.J., Silver(I)-catalyzed diastereoselective synthesis of anti-1,2-hydroxyboronates. Angew. Chem. Int. Ed. 54 (2015), 14141–14145.
    • (2015) Angew. Chem. Int. Ed. , vol.54 , pp. 14141-14145
    • Joannou, M.V.1    Moyer, B.S.2    Goldfogel, M.J.3    Meek, S.J.4
  • 96
    • 84978741653 scopus 로고    scopus 로고
    • Enantio- and diastereoselective 1,2-additions to a-ketoesters with diborylmethane and substituted 1,1-diborylalkanes
    • Murray, S.A., Green, J.C., Tailor, S.B., Meek, S.J., Enantio- and diastereoselective 1,2-additions to a-ketoesters with diborylmethane and substituted 1,1-diborylalkanes. Angew. Chem. Int. Ed. 55 (2016), 9065–9069.
    • (2016) Angew. Chem. Int. Ed. , vol.55 , pp. 9065-9069
    • Murray, S.A.1    Green, J.C.2    Tailor, S.B.3    Meek, S.J.4
  • 97
    • 0035904470 scopus 로고    scopus 로고
    • Room-temperature alkyl–alkyl Suzuki cross-coupling of alkyl bromides that possess β hydrogens
    • Netherton, M.R., Dai, C., Neuschütz, K., Fu, G.C., Room-temperature alkyl–alkyl Suzuki cross-coupling of alkyl bromides that possess β hydrogens. J. Am. Chem. Soc. 123 (2001), 10099–10100.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10099-10100
    • Netherton, M.R.1    Dai, C.2    Neuschütz, K.3    Fu, G.C.4
  • 98
    • 34547789922 scopus 로고    scopus 로고
    • Alkyl–alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature
    • Saito, B., Fu, G.C., Alkyl–alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature. J. Am. Chem. Soc. 129 (2007), 9602–9603.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9602-9603
    • Saito, B.1    Fu, G.C.2
  • 99
    • 84905277300 scopus 로고    scopus 로고
    • Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis
    • Hong, K., Liu, X., Morken, J.P., Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis. J. Am. Chem. Soc. 136 (2014), 10581–10584.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 10581-10584
    • Hong, K.1    Liu, X.2    Morken, J.P.3
  • 100
    • 84920266021 scopus 로고    scopus 로고
    • Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides
    • Potter, B., Szymaniak, A.A., Edelstein, E.K., Morken, J.P., Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides. J. Am. Chem. Soc. 136 (2014), 17918–17921.
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 17918-17921
    • Potter, B.1    Szymaniak, A.A.2    Edelstein, E.K.3    Morken, J.P.4
  • 101
    • 84977274838 scopus 로고    scopus 로고
    • Modular, catalytic enantioselective construction of quaternary carbon stereocentres by sequential cross-coupling reactions
    • Potter, B., Edelstein, E.K., Morken, J.P., Modular, catalytic enantioselective construction of quaternary carbon stereocentres by sequential cross-coupling reactions. Org. Lett. 18 (2016), 3286–3289.
    • (2016) Org. Lett. , vol.18 , pp. 3286-3289
    • Potter, B.1    Edelstein, E.K.2    Morken, J.P.3
  • 102
    • 84919662838 scopus 로고    scopus 로고
    • Copper-catalyzed/promoted cross-coupling of gem-diborylalkanes with nonactivated primary alkyl halides: an alternative route to alkylboronic esters
    • Zhang, Z.-Q., Yang, C.-T., Liang, L.-J., Xiao, B., Lu, X., Liu, J.-H., Sun, Y.-Y., Marder, T.B., Fu, Y., Copper-catalyzed/promoted cross-coupling of gem-diborylalkanes with nonactivated primary alkyl halides: an alternative route to alkylboronic esters. Org. Lett. 16 (2014), 6342–6345.
    • (2014) Org. Lett. , vol.16 , pp. 6342-6345
    • Zhang, Z.-Q.1    Yang, C.-T.2    Liang, L.-J.3    Xiao, B.4    Lu, X.5    Liu, J.-H.6    Sun, Y.-Y.7    Marder, T.B.8    Fu, Y.9
  • 104
    • 47749122232 scopus 로고    scopus 로고
    • Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis
    • Wiley-VCH
    • Berkessel, A., Groger, H., Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis. 2005, Wiley-VCH.
    • (2005)
    • Berkessel, A.1    Groger, H.2
  • 105
    • 0345661260 scopus 로고
    • Organoboron compounds. XIV. Polyfunctional catalysis by 8-quinolineboronic acid
    • Letsinger, R.L., Dandegaonker, S., Vullo, W.J., Morrison, J.D., Organoboron compounds. XIV. Polyfunctional catalysis by 8-quinolineboronic acid. J. Am. Chem. Soc. 85 (1963), 2223–2227.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2223-2227
    • Letsinger, R.L.1    Dandegaonker, S.2    Vullo, W.J.3    Morrison, J.D.4
  • 106
    • 84907379183 scopus 로고    scopus 로고
    • Boronic acid catalysis: an atom-economical platform for direct activation and functionalization of carboxylic acids and alcohols
    • For a review, see
    • For a review, seeZheng, H., Hall, D.G., Boronic acid catalysis: an atom-economical platform for direct activation and functionalization of carboxylic acids and alcohols. Aldrichim. Acta 47 (2014), 41–51.
    • (2014) Aldrichim. Acta , vol.47 , pp. 41-51
    • Zheng, H.1    Hall, D.G.2
  • 107
    • 84984903230 scopus 로고    scopus 로고
    • Dual catalysis using boronic acid and chiral amine: acyclic quaternary carbons via enantioselective alkylation of branched aldehydes with allylic alcohols
    • Mo, X., Hall, D.G., Dual catalysis using boronic acid and chiral amine: acyclic quaternary carbons via enantioselective alkylation of branched aldehydes with allylic alcohols. J. Am. Chem. Soc. 138 (2016), 10762–10765.
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 10762-10765
    • Mo, X.1    Hall, D.G.2
  • 108
    • 85017127150 scopus 로고    scopus 로고
    • Spectroscopic studies of the Chan-Lam amination: a mechanism-inspired solution to boronic ester reactivity
    • Vantourout, J.C., Miras, H.N., Isidro-Llobet, A., Sproules, S., Watson, A.J.B., Spectroscopic studies of the Chan-Lam amination: a mechanism-inspired solution to boronic ester reactivity. J. Am. Soc. Chem. 139 (2017), 4769–4779.
    • (2017) J. Am. Soc. Chem. , vol.139 , pp. 4769-4779
    • Vantourout, J.C.1    Miras, H.N.2    Isidro-Llobet, A.3    Sproules, S.4    Watson, A.J.B.5
  • 109
    • 84968902231 scopus 로고    scopus 로고
    • Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters: overcoming the aryl amine problem
    • Vantourout, J.C., Law, R.P., Isidro-Llobet, A., Atkinson, S.J., Watson, A.J.B., Chan–Evans–Lam amination of boronic acid pinacol (BPin) esters: overcoming the aryl amine problem. J. Org. Chem. 81 (2016), 3942–3950.
    • (2016) J. Org. Chem. , vol.81 , pp. 3942-3950
    • Vantourout, J.C.1    Law, R.P.2    Isidro-Llobet, A.3    Atkinson, S.J.4    Watson, A.J.B.5


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