메뉴 건너뛰기




Volumn 3, Issue 7, 2017, Pages 692-700

Transition-Metal Catalysis of Nucleophilic Substitution Reactions: A Radical Alternative to SN1 and SN2 Processes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; METAL COMPLEXES; SUBSTITUTION REACTIONS; TRANSITION METAL COMPOUNDS;

EID: 85026377426     PISSN: 23747943     EISSN: 23747951     Source Type: Journal    
DOI: 10.1021/acscentsci.7b00212     Document Type: Article
Times cited : (443)

References (73)
  • 2
    • 23044443893 scopus 로고    scopus 로고
    • Substitutions at Aliphatic Centers and Thermal Isomerizations/Rearrangements
    • University Science Books: Sausalito, CA, Chapter 11
    • Anslyn, E. V. and Dougherty, D. A. Substitutions at Aliphatic Centers and Thermal Isomerizations/Rearrangements. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; Chapter 11.
    • (2006) Modern Physical Organic Chemistry
    • Anslyn, E.V.1    Dougherty, D.A.2
  • 3
    • 44949230317 scopus 로고    scopus 로고
    • Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions
    • For examples of interesting exceptions (albeit with limited scope with respect to the nucleophile and the electrophile), see: Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions J. Am. Chem. Soc. 2008, 130, 7198-7199 10.1021/ja801514m
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 7198-7199
    • Reisman, S.E.1    Doyle, A.G.2    Jacobsen, E.N.3
  • 4
    • 85013074396 scopus 로고    scopus 로고
    • Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions
    • Lee, S.; Kaib, P. S. J.; List, B. Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions J. Am. Chem. Soc. 2017, 139, 2156-2159 10.1021/jacs.6b11993
    • (2017) J. Am. Chem. Soc. , vol.139 , pp. 2156-2159
    • Lee, S.1    Kaib, P.S.J.2    List, B.3
  • 7
  • 8
    • 84945933950 scopus 로고    scopus 로고
    • Tutorial on Oxidative Addition
    • For leading references, see: Labinger, J. A. Tutorial on Oxidative Addition Organometallics 2015, 34, 4784-4795 10.1021/acs.organomet.5b00565
    • (2015) Organometallics , vol.34 , pp. 4784-4795
    • Labinger, J.A.1
  • 9
    • 84858110887 scopus 로고    scopus 로고
    • Radicals in Transition Metal Catalyzed Reactions? Transition Metal Catalyzed Radical Reactions?: A Fruitful Interplay Anyway
    • For leading references, see: Jahn, U. Radicals in Transition Metal Catalyzed Reactions? Transition Metal Catalyzed Radical Reactions?: A Fruitful Interplay Anyway Top. Curr. Chem. 2011, 320, 323-452 10.1007/128-2011-288
    • (2011) Top. Curr. Chem. , vol.320 , pp. 323-452
    • Jahn, U.1
  • 11
    • 84903493026 scopus 로고    scopus 로고
    • 2 carbon centers
    • Knochel, P. Molander, G. A. Elsevier: Amsterdam
    • 2 carbon centers. In Comprehensive Organic Synthesis; Knochel, P.; Molander, G. A., Eds.; Elsevier: Amsterdam, 2014; Vol. 3, pp 392-464.
    • (2014) Comprehensive Organic Synthesis , vol.3 , pp. 392-464
    • Manolikakes, G.1
  • 12
    • 85018502103 scopus 로고    scopus 로고
    • Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry
    • Choi, J.; Fu, G. C. Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry Science 2017, 356, eaaf7230 10.1126/science.aaf7230
    • (2017) Science , vol.356 , pp. eaaf7230
    • Choi, J.1    Fu, G.C.2
  • 15
    • 33645524221 scopus 로고    scopus 로고
    • Palladium-Catalyzed Cross-Coupling Reactions of Unactivated Alkyl Electrophiles with Organometallic Compounds
    • For leading references to synthetic and mechanistic studies, see: Netherton, M. R.; Fu, G. C. Palladium-Catalyzed Cross-Coupling Reactions of Unactivated Alkyl Electrophiles with Organometallic Compounds. Topics in Organometallic Chemistry: Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: New York, 2005; pp 85-108.
    • (2005) Topics in Organometallic Chemistry: Palladium in Organic Synthesis , pp. 85-108
    • Netherton, M.R.1    Fu, G.C.2
  • 16
    • 84900544451 scopus 로고    scopus 로고
    • Recent advances in homogeneous nickel catalysis
    • For a discussion and leading references, see: Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Recent advances in homogeneous nickel catalysis Nature 2014, 509, 299-309 10.1038/nature13274
    • (2014) Nature , vol.509 , pp. 299-309
    • Tasker, S.Z.1    Standley, E.A.2    Jamison, T.F.3
  • 18
    • 0344861888 scopus 로고    scopus 로고
    • Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides
    • Organozinc nucleophiles
    • Organozinc nucleophiles: Zhou, J.; Fu, G. C. Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides J. Am. Chem. Soc. 2003, 125, 14726-14727 10.1021/ja0389366
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14726-14727
    • Zhou, J.1    Fu, G.C.2
  • 19
    • 1042288193 scopus 로고    scopus 로고
    • Suzuki Cross-Couplings of Unactivated Secondary Alkyl Bromides and Iodides
    • Organoboron nucleophiles
    • Organoboron nucleophiles: Zhou, J.; Fu, G. C. Suzuki Cross-Couplings of Unactivated Secondary Alkyl Bromides and Iodides J. Am. Chem. Soc. 2004, 126, 1340-1341 10.1021/ja039889k
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 1340-1341
    • Zhou, J.1    Fu, G.C.2
  • 20
    • 77956500677 scopus 로고    scopus 로고
    • Alkyl-Alkyl Suzuki Cross-Coupling of Unactivated Secondary Alkyl Chlorides
    • Lu, Z.; Fu, G. C. Alkyl-Alkyl Suzuki Cross-Coupling of Unactivated Secondary Alkyl Chlorides Angew. Chem., Int. Ed. 2010, 49, 6676-6678 10.1002/anie.201003272
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6676-6678
    • Lu, Z.1    Fu, G.C.2
  • 21
    • 33646447380 scopus 로고    scopus 로고
    • Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids
    • See also
    • See also: González-Bobes, F.; Fu, G. C. Amino Alcohols as Ligands for Nickel-Catalyzed Suzuki Reactions of Unactivated Alkyl Halides, Including Secondary Alkyl Chlorides, with Arylboronic Acids J. Am. Chem. Soc. 2006, 128, 5360-5361 10.1021/ja0613761
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 5360-5361
    • González-Bobes, F.1    Fu, G.C.2
  • 22
    • 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. 2007, 129, 9602-9603 10.1021/ja074008l
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9602-9603
    • Saito, B.1    Fu, G.C.2
  • 23
    • 3042542346 scopus 로고    scopus 로고
    • Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl Bromides
    • Organosilicon nucleophiles
    • Organosilicon nucleophiles: Powell, D. A.; Fu, G. C. Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl Bromides J. Am. Chem. Soc. 2004, 126, 7788-7789 10.1021/ja047433c
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 7788-7789
    • Powell, D.A.1    Fu, G.C.2
  • 24
    • 34250821753 scopus 로고    scopus 로고
    • Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex
    • See also
    • See also: Strotman, N. A.; Sommer, S.; Fu, G. C. Hiyama Reactions of Activated and Unactivated Secondary Alkyl Halides Catalyzed by a Nickel/Norephedrine Complex Angew. Chem., Int. Ed. 2007, 46, 3556-3558 10.1002/anie.200700440
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 3556-3558
    • Strotman, N.A.1    Sommer, S.2    Fu, G.C.3
  • 25
    • 12944309312 scopus 로고    scopus 로고
    • Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents
    • Organotin nucleophiles
    • Organotin nucleophiles: Powell, D. A.; Maki, T.; Fu, G. C. Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents J. Am. Chem. Soc. 2005, 127, 510-511 10.1021/ja0436300
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 510-511
    • Powell, D.A.1    Maki, T.2    Fu, G.C.3
  • 26
    • 84913539477 scopus 로고    scopus 로고
    • Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation
    • For a mechanistic study that implicates radical intermediates in a nickel-catalyzed enantioconvergent coupling of an activated electrophile, see: Schley, N. D.; Fu, G. C. Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation J. Am. Chem. Soc. 2014, 136, 16588-16593 10.1021/ja508718m
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 16588-16593
    • Schley, N.D.1    Fu, G.C.2
  • 27
    • 84872563127 scopus 로고    scopus 로고
    • Nickel-Catalyzed Carbon-Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations
    • Zultanski, S. L.; Fu, G. C. Nickel-Catalyzed Carbon-Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations J. Am. Chem. Soc. 2013, 135, 624-627 10.1021/ja311669p
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 624-627
    • Zultanski, S.L.1    Fu, G.C.2
  • 28
    • 79251471974 scopus 로고    scopus 로고
    • Enantioselective allylic substitutions with carbon nucleophiles
    • Ojima, I. John Wiley & Sons: Hoboken, NJ
    • Helmchen, G.; Kazmaier, U.; Förster, S. Enantioselective allylic substitutions with carbon nucleophiles. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; John Wiley & Sons: Hoboken, NJ, 2010; pp 497-641.
    • (2010) Catalytic Asymmetric Synthesis , pp. 497-641
    • Helmchen, G.1    Kazmaier, U.2    Förster, S.3
  • 29
    • 84941112141 scopus 로고    scopus 로고
    • Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents to Construct C-C Bonds
    • For leading references, see: Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds Chem. Rev. 2015, 115, 9587-9652 10.1021/acs.chemrev.5b00162
    • (2015) Chem. Rev. , vol.115 , pp. 9587-9652
    • Cherney, A.H.1    Kadunce, N.T.2    Reisman, S.E.3
  • 30
    • 16844363000 scopus 로고    scopus 로고
    • Asymmetric Nickel-Catalyzed Negishi Cross-Couplings of Secondary α-Bromo Amides with Organozinc Reagents
    • Fischer, C.; Fu, G. C. Asymmetric Nickel-Catalyzed Negishi Cross-Couplings of Secondary α-Bromo Amides with Organozinc Reagents J. Am. Chem. Soc. 2005, 127, 4594-4595 10.1021/ja0506509
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4594-4595
    • Fischer, C.1    Fu, G.C.2
  • 31
    • 58249115061 scopus 로고    scopus 로고
    • Catalytic Asymmetric Cross-Couplings of Racemic α-Bromoketones with Arylzinc Reagents
    • See also: Lundin, P. M.; Esquivias, J.; Fu, G. C. Catalytic Asymmetric Cross-Couplings of Racemic α-Bromoketones with Arylzinc Reagents Angew. Chem., Int. Ed. 2009, 48, 154-156 10.1002/anie.200804888
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 154-156
    • Lundin, P.M.1    Esquivias, J.2    Fu, G.C.3
  • 32
    • 84897970502 scopus 로고    scopus 로고
    • Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones
    • Liang, Y.; Fu, G. C. Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones J. Am. Chem. Soc. 2014, 136, 5520-5524 10.1021/ja501815p
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 5520-5524
    • Liang, Y.1    Fu, G.C.2
  • 33
    • 84867556242 scopus 로고    scopus 로고
    • Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents
    • Benzylic halides
    • Benzylic halides: Binder, J. T.; Cordier, C. J.; Fu, G. C. Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents J. Am. Chem. Soc. 2012, 134, 17003-17006 10.1021/ja308460z
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 17003-17006
    • Binder, J.T.1    Cordier, C.J.2    Fu, G.C.3
  • 34
    • 23044496800 scopus 로고    scopus 로고
    • Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic Halides
    • See also: Arp, F. O.; Fu, G. C. Catalytic Enantioselective Negishi Reactions of Racemic Secondary Benzylic Halides J. Am. Chem. Soc. 2005, 127, 10482-10483 10.1021/ja053751f
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10482-10483
    • Arp, F.O.1    Fu, G.C.2
  • 35
    • 84887750453 scopus 로고    scopus 로고
    • Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
    • Do, H.-Q.; Chandrashekar, E. R. R.; Fu, G. C. Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes J. Am. Chem. Soc. 2013, 135, 16288-16291 10.1021/ja408561b
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 16288-16291
    • Do, H.-Q.1    Chandrashekar, E.R.R.2    Fu, G.C.3
  • 36
    • 40949123444 scopus 로고    scopus 로고
    • Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs
    • Allylic halides
    • Allylic halides: Son, S.; Fu, G. C. Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs J. Am. Chem. Soc. 2008, 130, 2756-2757 10.1021/ja800103z
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2756-2757
    • Son, S.1    Fu, G.C.2
  • 37
    • 84863116000 scopus 로고    scopus 로고
    • Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
    • Propargylic electrophiles
    • Propargylic electrophiles: Oelke, A. J.; Sun, J.; Fu, G. C. Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group J. Am. Chem. Soc. 2012, 134, 2966-2969 10.1021/ja300031w
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 2966-2969
    • Oelke, A.J.1    Sun, J.2    Fu, G.C.3
  • 38
    • 52449132069 scopus 로고    scopus 로고
    • Nickel-Catalyzed Asymmetric Cross-Couplings of Racemic Propargylic Halides with Arylzinc Reagents
    • See also: Smith, S. W.; Fu, G. C. Nickel-Catalyzed Asymmetric Cross-Couplings of Racemic Propargylic Halides with Arylzinc Reagents J. Am. Chem. Soc. 2008, 130, 12645-12647 10.1021/ja805165y
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12645-12647
    • Smith, S.W.1    Fu, G.C.2
  • 39
    • 84861902827 scopus 로고    scopus 로고
    • Catalytic Asymmetric Synthesis of Secondary Nitriles via Stereoconvergent Negishi Arylations and Alkenylations of Racemic α-Bromonitriles
    • Halonitriles
    • α-Halonitriles: Choi, J.; Fu, G. C. Catalytic Asymmetric Synthesis of Secondary Nitriles via Stereoconvergent Negishi Arylations and Alkenylations of Racemic α-Bromonitriles J. Am. Chem. Soc. 2012, 134, 9102-9105 10.1021/ja303442q
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 9102-9105
    • Choi, J.1    Fu, G.C.2
  • 40
    • 84856021728 scopus 로고    scopus 로고
    • Total Synthesis of Carolacton, a Highly Potent Biofilm Inhibitor
    • Carolacton
    • Carolacton: Schmidt, T.; Kirschning, A. Total Synthesis of Carolacton, a Highly Potent Biofilm Inhibitor Angew. Chem., Int. Ed. 2012, 51, 1063-1066 10.1002/anie.201106762
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 1063-1066
    • Schmidt, T.1    Kirschning, A.2
  • 42
  • 43
    • 77950503735 scopus 로고    scopus 로고
    • Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones
    • Organomagnesium nucleophiles
    • Organomagnesium nucleophiles: Lou, S.; Fu, G. C. Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones J. Am. Chem. Soc. 2010, 132, 1264-1266 10.1021/ja909689t
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1264-1266
    • Lou, S.1    Fu, G.C.2
  • 44
    • 41449104100 scopus 로고    scopus 로고
    • Catalytic Asymmetric Hiyama Cross-Couplings of Racemic α-Bromo Esters
    • Organosilicon nucleophiles
    • Organosilicon nucleophiles: Dai, X.; Strotman, N. A.; Fu, G. C. Catalytic Asymmetric Hiyama Cross-Couplings of Racemic α-Bromo Esters J. Am. Chem. Soc. 2008, 130, 3302-3303 10.1021/ja8009428
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 3302-3303
    • Dai, X.1    Strotman, N.A.2    Fu, G.C.3
  • 45
    • 77950807083 scopus 로고    scopus 로고
    • Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents
    • Organozirconium nucleophiles
    • Organozirconium nucleophiles: Lou, S.; Fu, G. C. Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents J. Am. Chem. Soc. 2010, 132, 5010-5011 10.1021/ja1017046
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5010-5011
    • Lou, S.1    Fu, G.C.2
  • 46
    • 84906766693 scopus 로고    scopus 로고
    • Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones
    • See also: Choi, J.; Martín-Gago, P.; Fu, G. C. Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones J. Am. Chem. Soc. 2014, 136, 12161-12165 10.1021/ja506885s
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 12161-12165
    • Choi, J.1    Martín-Gago, P.2    Fu, G.C.3
  • 47
    • 77955573357 scopus 로고    scopus 로고
    • Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides
    • Organoboron nucleophiles
    • Organoboron nucleophiles: Lundin, P. M.; Fu, G. C. Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides J. Am. Chem. Soc. 2010, 132, 11027-11029 10.1021/ja105148g
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11027-11029
    • Lundin, P.M.1    Fu, G.C.2
  • 48
    • 44349182541 scopus 로고    scopus 로고
    • Enantioselective Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Homobenzylic Halides
    • Aromatic ring
    • Aromatic ring: Saito, B.; Fu, G. C. Enantioselective Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Homobenzylic Halides J. Am. Chem. Soc. 2008, 130, 6694-6695 10.1021/ja8013677
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 6694-6695
    • Saito, B.1    Fu, G.C.2
  • 49
    • 77956083484 scopus 로고    scopus 로고
    • Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
    • Carbonyl
    • Carbonyl: Owston, N. A.; Fu, G. C. Asymmetric Alkyl-Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins J. Am. Chem. Soc. 2010, 132, 11908-11909 10.1021/ja105924f
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11908-11909
    • Owston, N.A.1    Fu, G.C.2
  • 50
    • 80053339478 scopus 로고    scopus 로고
    • Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings
    • See also: Zultanski, S. L.; Fu, G. C. Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings J. Am. Chem. Soc. 2011, 133, 15362-15364 10.1021/ja2079515
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 15362-15364
    • Zultanski, S.L.1    Fu, G.C.2
  • 51
    • 79957675617 scopus 로고    scopus 로고
    • Stereoconvergent Amine-Directed Alkyl-Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
    • Nitrogen
    • Nitrogen: Lu, Z.; Wilsily, A.; Fu, G. C. Stereoconvergent Amine-Directed Alkyl-Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides J. Am. Chem. Soc. 2011, 133, 8154-8157 10.1021/ja203560q
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8154-8157
    • Lu, Z.1    Wilsily, A.2    Fu, G.C.3
  • 52
    • 84859355289 scopus 로고    scopus 로고
    • New Directing Groups for Metal-Catalyzed Asymmetric Carbon-Carbon Bond-Forming Processes: Stereoconvergent Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles
    • Sulfonamide
    • Sulfonamide: Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. New Directing Groups for Metal-Catalyzed Asymmetric Carbon-Carbon Bond-Forming Processes: Stereoconvergent Alkyl-Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles J. Am. Chem. Soc. 2012, 134, 5794-5797 10.1021/ja301612y
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 5794-5797
    • Wilsily, A.1    Tramutola, F.2    Owston, N.A.3    Fu, G.C.4
  • 53
    • 84938894515 scopus 로고    scopus 로고
    • 3 and an Alkyl Group
    • 3 and an Alkyl Group J. Am. Chem. Soc. 2015, 137, 9523-9526 10.1021/jacs.5b04725
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 9523-9526
    • Liang, Y.1    Fu, G.C.2
  • 54
    • 85003022498 scopus 로고    scopus 로고
    • A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters
    • Schmidt, J.; Choi, J.; Liu, A. T.; Slusarczyk, M.; Fu, G. C. A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters Science 2016, 354, 1265-1269 10.1126/science.aai8611
    • (2016) Science , vol.354 , pp. 1265-1269
    • Schmidt, J.1    Choi, J.2    Liu, A.T.3    Slusarczyk, M.4    Fu, G.C.5
  • 57
    • 84863469858 scopus 로고    scopus 로고
    • Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, to Generate Carbon-Boron Bonds
    • Boron nucleophile
    • Boron nucleophile: Dudnik, A. S.; Fu, G. C. Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds J. Am. Chem. Soc. 2012, 134, 10693-10697 10.1021/ja304068t
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 10693-10697
    • Dudnik, A.S.1    Fu, G.C.2
  • 58
    • 84971379323 scopus 로고    scopus 로고
    • Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles
    • Silicon nucleophile
    • Silicon nucleophile: Chu, C. K.; Liang, Y.; Fu, G. C. Silicon-Carbon Bond Formation via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Unactivated Secondary and Tertiary Alkyl Electrophiles J. Am. Chem. Soc. 2016, 138, 6404-6407 10.1021/jacs.6b03465
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 6404-6407
    • Chu, C.K.1    Liang, Y.2    Fu, G.C.3
  • 60
    • 84856693018 scopus 로고    scopus 로고
    • Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides
    • Ito, H.; Kubota, K. Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides Org. Lett. 2012, 14, 890-893 10.1021/ol203413w
    • (2012) Org. Lett. , vol.14 , pp. 890-893
    • Ito, H.1    Kubota, K.2
  • 62
    • 84857360028 scopus 로고    scopus 로고
    • Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties
    • There were isolated reports of N-alkylations of amines with unactivated alkyl halides that proceed in the presence of a substoichiometric quantity of a transition metal. For example, see: (165 °C; primary alkyl bromide)
    • There were isolated reports of N-alkylations of amines with unactivated alkyl halides that proceed in the presence of a substoichiometric quantity of a transition metal. For example, see: Aydin, A.; Kaya, I. Synthesis and characterization of yellow and green light emitting novel polymers containing carbazole and electroactive moieties Electrochim. Acta 2012, 65, 104-114 (165 °C; primary alkyl bromide) 10.1016/j.electacta.2012.01.028
    • (2012) Electrochim. Acta , vol.65 , pp. 104-114
    • Aydin, A.1    Kaya, I.2
  • 63
    • 77956094139 scopus 로고    scopus 로고
    • The synthesis and electrochemical properties of cathodic-anodic composite electrochromic materials
    • (80 °C; primary alkyl bromide)
    • Tu, X.; Fu, X.; Jiang, Q.; Liu, Z.; Chen, G. The synthesis and electrochemical properties of cathodic-anodic composite electrochromic materials Dyes Pigm. 2011, 88, 39-43 (80 °C; primary alkyl bromide) 10.1016/j.dyepig.2010.04.012
    • (2011) Dyes Pigm. , vol.88 , pp. 39-43
    • Tu, X.1    Fu, X.2    Jiang, Q.3    Liu, Z.4    Chen, G.5
  • 64
    • 20344374956 scopus 로고    scopus 로고
    • The direct synthesis of tertiary amines with three different substituents via the reaction of primary amines, alkyl halides, and α-chlorine substituted allylsilanes catalyzed by Lewis acids
    • (83 °C; primary alkyl bromide)
    • Kozuka, M.; Tsuchida, T.; Mitani, M. The direct synthesis of tertiary amines with three different substituents via the reaction of primary amines, alkyl halides, and α-chlorine substituted allylsilanes catalyzed by Lewis acids Tetrahedron Lett. 2005, 46, 4527-4530 (83 °C; primary alkyl bromide) 10.1016/j.tetlet.2005.05.022
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4527-4530
    • Kozuka, M.1    Tsuchida, T.2    Mitani, M.3
  • 65
    • 84868238205 scopus 로고    scopus 로고
    • Photoinduced Ullmann C-N coupling: Demonstrating the viability of a radical pathway
    • Creutz, S. E.; Lotito, K. J.; Fu, G. C.; Peters, J. C. Photoinduced Ullmann C-N coupling: demonstrating the viability of a radical pathway Science 2012, 338, 647-651 10.1126/science.1226458
    • (2012) Science , vol.338 , pp. 647-651
    • Creutz, S.E.1    Lotito, K.J.2    Fu, G.C.3    Peters, J.C.4
  • 66
  • 67
    • 84877695378 scopus 로고    scopus 로고
    • Transition-metal-catalyzed alkylations of amines with alkyl halides: Photoinduced, copper-catalyzed couplings of carbazoles
    • Bissember, A. C.; Lundgren, R. J.; Creutz, S. E.; Peters, J. C.; Fu, G. C. Transition-metal-catalyzed alkylations of amines with alkyl halides: photoinduced, copper-catalyzed couplings of carbazoles Angew. Chem., Int. Ed. 2013, 52, 5129-5133 10.1002/anie.201301202
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 5129-5133
    • Bissember, A.C.1    Lundgren, R.J.2    Creutz, S.E.3    Peters, J.C.4    Fu, G.C.5
  • 68
    • 84969617464 scopus 로고    scopus 로고
    • Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?
    • For example, amides are the most frequently occurring functional group in the IBEX database of patents in the area of medicinal chemistry
    • For example, amides are the most frequently occurring functional group in the IBEX database of patents in the area of medicinal chemistry: 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. 2016, 59, 4443-4458 10.1021/acs.jmedchem.5b01409
    • (2016) J. Med. Chem. , vol.59 , pp. 4443-4458
    • Brown, D.G.1    Boström, J.2
  • 69
    • 84893773566 scopus 로고    scopus 로고
    • Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature
    • Do, H.-Q.; Bachman, S.; Bissember, A. C.; Peters, J. C.; Fu, G. C. Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature J. Am. Chem. Soc. 2014, 136, 2162-2167 10.1021/ja4126609
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 2162-2167
    • Do, H.-Q.1    Bachman, S.2    Bissember, A.C.3    Peters, J.C.4    Fu, G.C.5
  • 70
    • 84957899492 scopus 로고    scopus 로고
    • Asymmetric copper-catalyzed C-N cross-couplings induced by visible light
    • (mechanistic studies of this process are underway)
    • Kainz, Q. M.; Matier, C. M.; Bartoszewicz, A.; Zultanski, S. L.; Peters, J. C.; Fu, G. C. Asymmetric copper-catalyzed C-N cross-couplings induced by visible light Science 2016, 351, 681-684 (mechanistic studies of this process are underway) 10.1126/science.aad8313
    • (2016) Science , vol.351 , pp. 681-684
    • Kainz, Q.M.1    Matier, C.M.2    Bartoszewicz, A.3    Zultanski, S.L.4    Peters, J.C.5    Fu, G.C.6
  • 72
    • 84921490704 scopus 로고    scopus 로고
    • Catalytic enantioselective synthesis of quaternary carbon stereocentres
    • Quasdorf, K. W.; Overman, L. E. Catalytic enantioselective synthesis of quaternary carbon stereocentres Nature 2014, 516, 181-191 10.1038/nature14007
    • (2014) Nature , vol.516 , pp. 181-191
    • Quasdorf, K.W.1    Overman, L.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.