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Molander, G. A.: 2020 Science of Synthesis, 2019/4: Dual Catalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-231-00041
Dual Catalysis in Organic Synthesis 1

1.1.4 Iridium/Zinc and Iridium/Copper Dual Catalysis

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Editor: Molander, G. A.

Authors: Barriault, L. ; Bhoyare, V. W.; Hashmi, A. S. K. ; He, R.; Huo, X.; Kim, U B.; Lee, S.-g.; Molander, G. A.; Muralirajan, K.; Nakao, Y.; Patil, N. T.; Primer, D. N.; Riant, O.; Rohe, S.; Rout, S. K.; Rueping, M. ; Shi, X.; Tathe, A. G.; Tellis, J. C.; Wang, J.; Zhang, W. ; Zidan, M. 

Title: Dual Catalysis in Organic Synthesis 1

Print ISBN: 9783132429765; Online ISBN: 9783132429802; Book DOI: 10.1055/b-006-164899

1st edition © 2020. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

Synergistic bimetallic catalysis is gaining increasing attention due to its advantages over traditional catalytic methodologies. These advantages include double activation, accurate control of reaction sites, double stereochemical control, and potential in stereodivergent synthesis. This review documents advances in the field and provides an up-to-date overview of recent developments in the use of iridium/zinc and iridium/copper catalyst systems.

Key words

dual catalysis - transition-metal catalysis - iridium - zinc - copper - synergistic bimetallic catalysis - stereodivergence - allylation - hydroamination - cyclization
 
  • 1 Crabtree RH. The Organometallic Chemistry of the Transition Metals. Wiley; Hoboken, NJ 2005
    Google Scholar
  • 2 Catalytic Asymmetric Synthesis. Ojima I. Wiley; Hoboken, NJ 2009
    Google Scholar
  • 3 Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books; Sausalito, CA 2010
    Google Scholar
  • 5 Privileged Chiral Ligands and Catalysts. Zhou Q.-L. Wiley-VCH; Weinheim, Germany 2011
    Google Scholar
  • 6 Yoon TP, Jacobsen EN. Science (Washington, D. C.). 2003; 299: 1691
    Google Scholar
  • 7 Schindler CS, Jacobsen EN. Science (Washington, D. C.). 2013; 340: 1052
    Google Scholar
  • 8 Oliveira MT, Luparia M, Audisio D, Maulide N. Angew. Chem. Int. Ed.. 2013; 52: 13149
    Google Scholar
  • 10 Krautwald S, Carreira EM. J. Am. Chem. Soc.. 2017; 139: 5627
    Google Scholar
  • 11 Bihani M, Zhao JC.-G. Adv. Synth. Catal.. 2017; 359: 534
    Google Scholar
  • 12 Beletskaya IP, Nájera C, Yus M. Chem. Rev.. 2018; 118: 5080
    Google Scholar
  • 13 van den Beuken EK, Feringa BL. Tetrahedron. 1998; 54: 12985
    Google Scholar
  • 14 Shibasaki M, Yoshikawa N. Chem. Rev.. 2002; 102: 2187
    Google Scholar
  • 15 Shibasaki M, Matsunaga S. Chem. Soc. Rev.. 2006; 35: 269
    Google Scholar
  • 16 Shibasaki M, Kanai M, Matsunaga S, Kumagai N. Acc. Chem. Res.. 2009; 42: 1117
    Google Scholar
  • 19 Bratko I, Gómez M. Dalton Trans.. 2013; 42: 10664
    Google Scholar
  • 21 Fu J, Huo X, Li B, Zhang W. Org. Biomol. Chem.. 2017; 15: 9747
    Google Scholar
  • 23 Dieck HA, Heck FR. J. Organomet. Chem.. 1975; 93: 259
    Google Scholar
  • 24 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett.. 1975; 16: 4467
    Google Scholar
  • 26 Casalnuovo AL, Calabrese JC, Milstein D. J. Am. Chem. Soc.. 1988; 110: 6738
    Google Scholar
  • 27 Trost BM, Van Vranken DL. Chem. Rev.. 1996; 96: 395
    Google Scholar
  • 28 Bartels B, Helmchen G. Chem. Commun. (Cambridge). 1999; 741
    Google Scholar
  • 30 Braun M, Meier T. Angew. Chem. Int. Ed.. 2006; 45: 6952
    Google Scholar
  • 31 Mohr JT, Stoltz BM. Chem.–Asian J.. 2007; 2: 1476
    Google Scholar
  • 32 Chi Y, Scroggins ST, Fréchet JMJ. J. Am. Chem. Soc.. 2008; 130: 6322
    Google Scholar
  • 33 Weaver JD, Recio III A, Grenning AJ, Tunge JA. Chem. Rev.. 2011; 111: 1846
    Google Scholar
  • 35 Carroll MP, Guiry PJ. Chem. Soc. Rev.. 2014; 43: 819
    Google Scholar
  • 37 Butt N, Yang G, Zhang W. Chem. Rec.. 2016; 16: 2687
    Google Scholar
  • 38 Grange RL, Clizbe EA, Evans PA. Synthesis. 2016; 48: 2911
    Google Scholar
  • 39 Helmchen G, Dahnz A, Dübon P, Schelwies M, Weihofen R. Chem. Commun. (Cambridge). 2007; 675
    Google Scholar
  • 40 Hartwig JF, Stanley LM. Acc. Chem. Res.. 2010; 43: 1461
    Google Scholar
  • 41 Liu W.-B, Xia J.-B, You S.-L. Top. Organomet. Chem.. 2011; 38: 155
    Google Scholar
  • 42 Helmchen G, Molecular Catalysts: Structure and Functional Design. Gade LH, Hofmann P. Wiley-VCH Weinheim, Germany 2014; 239
    Google Scholar
  • 44 Tang H, Huo X, Meng Q, Zhang W. Acta Chim. Sin. (Engl. Ed.). 2016; 74: 219
    Google Scholar
  • 46 Yang Z.-P, Jiang R, Zheng C, You S.-L. J. Am. Chem. Soc.. 2018; 140: 3114
    Google Scholar
  • 47 Kanayama T, Yoshida K, Miyabe H, Kimachi T, Takemoto Y. J. Org. Chem.. 2003; 68: 6197
    Google Scholar
  • 48 Kanayama T, Yoshida K, Miyabe H, Takemoto Y. Angew. Chem. Int. Ed.. 2003; 42: 2054
    Google Scholar
  • 49 Chen W, Hartwig JF. J. Am. Chem. Soc.. 2013; 135: 2068
    Google Scholar
  • 50 Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science (Washington, D. C.). 2013; 340: 1065
    Google Scholar
  • 51 Næsborg L, Halskov KS, Tur F, Mønsted SMN, Jørgensen KA. Angew. Chem. Int. Ed.. 2015; 54: 10193
    Google Scholar
  • 52 Sandmeier T, Krautwald S, Zipfel H. F, Carreira EM. Angew. Chem. Int. Ed.. 2015; 54: 14363
    Google Scholar
  • 53 Jiang X, Beiger JJ, Hartwig JF. J. Am. Chem. Soc.. 2017; 139: 87
    Google Scholar
  • 54 Chen W, Hartwig JF. J. Am. Chem. Soc.. 2014; 136: 377
    Google Scholar
  • 55 Fu Z, Deng N, Su S.-N, Li H, Li R.-Z, Zhang X, Liu J, Niu D. Angew. Chem. Int. Ed.. 2018; 57: 15217
    Google Scholar
  • 56 Stork G, Burgstahler AW. J. Am. Chem. Soc.. 1955; 77: 5068
    Google Scholar
  • 57 Eschenmoser A, Ruzicka L, Jeger O, Arigoni D. Helv. Chim. Acta. 1955; 38: 1890
    Google Scholar
  • 58 Stadler PA, Eschenmoser A, Schinz H, Stork G. Helv. Chim. Acta. 1957; 40: 2191
    Google Scholar
  • 59 Eschenmoser A, Arigoni D. Helv. Chim. Acta. 2005; 88: 3011
    Google Scholar
  • 60 Schafroth MA, Sarlah D, Krautwald S, Carreira EM. J. Am. Chem. Soc.. 2012; 134: 20276
    Google Scholar
  • 61 Schafroth MA, Rummelt SM, Sarlah D, Carreira EM. Org. Lett.. 2017; 19: 3235
    Google Scholar
  • 62 Jeker OF, Kravina AG, Carreira EM. Angew. Chem. Int. Ed.. 2013; 52: 12166
    Google Scholar
  • 63 Hamilton JY, Rössler SL, Carreira EM. J. Am. Chem. Soc.. 2017; 139: 8082
    Google Scholar
  • 64 Rössler SL, Schreib BS, Ginterseder M, Hamilton JY, Carreira EM. Org. Lett.. 2017; 19: 5533
    Google Scholar
  • 65 Tsuji J, Takahashi H, Morikawa M. Tetrahedron Lett.. 1965; 6: 4387
    Google Scholar
  • 66 Trost BM, Strege PE. J. Am. Chem. Soc.. 1977; 99: 1649
    Google Scholar
  • 67 Sempere Y, Carreira EM. Angew. Chem. Int. Ed.. 2018; 57: 7654
    Google Scholar
  • 68 Ramulu BJ, Nagaraju A, Chowdhury S, Koley S, Singh MS. Adv. Synth. Catal.. 2015; 357: 530
    Google Scholar
  • 69 Huo X, He R, Zhang X, Zhang W. J. Am. Chem. Soc.. 2016; 138: 11093
    Google Scholar
  • 70 He R, Liu P, Huo X, Zhang W. Org. Lett.. 2017; 19: 5513
    Google Scholar
  • 71 Zhan M, Li R.-Z, Mou Z.-D, Cao C.-G, Liu J, Chen Y.-W, Niu D. ACS Catal.. 2016; 6: 3381
    Google Scholar
  • 72 Nájera C, Sansano JM. Curr. Org. Chem.. 2003; 7: 1105
    Google Scholar
  • 74 Husinec S, Savic V. Tetrahedron: Asymmetry. 2005; 16: 2047
    Google Scholar
  • 75 Nájera C, Sansano JM. Angew. Chem. Int. Ed.. 2005; 44: 6272
    Google Scholar
  • 76 Pandey G, Banerjee P, Gadre SR. Chem. Rev.. 2006; 106: 4484
    Google Scholar
  • 77 Adrio J, Carretero JC. Chem. Commun. (Cambridge). 2011; 47: 6784
    Google Scholar
  • 78 Nájera C, Sansano JM. Monatsh. Chem.. 2011; 142: 659
    Google Scholar
  • 79 Adrio J, Carretero JC. Chem. Commun. (Cambridge). 2014; 50: 12434
    Google Scholar
  • 80 Nájera C, Sansano JM. J. Organomet. Chem.. 2014; 771: 78
    Google Scholar
  • 81 Narayan R, Potowski M, Jia Z.-J, Antonchick AP, Waldmann H. Acc. Chem. Res.. 2014; 47: 1296
    Google Scholar
  • 82 Grigg R, Montgomery J, Somasunderam A. Tetrahedron. 1992; 48: 10431
    Google Scholar
  • 83 Huo X, He R, Fu J, Zhang J, Yang G, Zhang W. J. Am. Chem. Soc.. 2017; 139: 9819
    Google Scholar
  • 84 Trost BM, Machacek MR, Aponick A. Acc. Chem. Res.. 2006; 39: 747
    Google Scholar
  • 85 Behenna DC, Mohr JT, Sherden NH, Marinescu SC, Harned AM, Tani K, Seto M, Ma S, Novák Z, Krout MR, McFadden RM, Roizen JL, Enquist Jr. JA, White DE, Levine SR, Petrova KV, Iwashita A, Virgil SC, Stoltz BM. Chem.–Eur. J.. 2011; 17: 14199
    Google Scholar
  • 86 Sakaguchi K, Suzuki H, Ohfune Y. Chirality. 2001; 13: 357
    Google Scholar
  • 87 Sakaguchi K, Yamamoto M, Kawamoto T, Yamada T, Shinada T, Shimamoto K, Ohfune Y. Tetrahedron Lett.. 2004; 45: 5869
    Google Scholar
  • 88 Huo X, Zhang J, Fu J, He R, Zhang W. J. Am. Chem. Soc.. 2018; 140: 2080
    Google Scholar
  • 89 Wei L, Zhu Q, Xu S.-M, Chang X, Wang C.-J. J. Am. Chem. Soc.. 2018; 140: 1508
    Google Scholar
  • 90 Zhang J, Huo X, Li B, Chen Z, Zou Y, Sun Z, Zhang W. Adv. Synth. Catal.. 2019; 361: 1130
    Google Scholar
  • 91 Jiang X, Boehm P, Hartwig JF. J. Am. Chem. Soc.. 2018; 140: 1239
    Google Scholar