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Fernández, E. et al.: 2021 Science of Synthesis, 2021/2: Knowledge Updates 2021/2 DOI: 10.1055/sos-SD-106-00205
Knowledge Updates 2021/2

6.1.43 Product Subclass 43: Azaborines (Borazines)

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Book

Editors: Fernández, E.; Huang, Z.; Jiang, X.; Koch, G.; Marschner, C.; Wang, M.

Authors: Chand, K. ; Davies, G. H. M.; Dorairaj, D. P.; Guo, R.; Hsu, S. C. N. ; Isovitsch, R.; Jiang, X.; Růžička, A.; Sirvinskas, M.; Takeda, N.; Trofimova, A.; Umesh; Vrána, J.; Wang, M.; Wisniewski, S. R.; Xiong, Y.; Ye, Z.-S.; Yudin, A. K.; Zhang, G. Z. 

Title: Knowledge Updates 2021/2

Print ISBN: 9783132442061; Online ISBN: 9783132442085; Book DOI: 10.1055/b000000477

1st edition © 2021 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

Science of Synthesis Knowledge Updates



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

Azaborines (or borazines) represent an interesting class of heterocycles incorporating a boron–nitrogen structural motif within an aromatic ring system. This creates a system that is isosteric to traditional all-carbon ring systems, as the lone pair on nitrogen can donate into the empty orbital at boron to afford aromatic properties. Reviewed herein are synthetic strategies to access mono- and bicyclic azaborine cores, along with subsequent functionalization strategies, some of which are uniquely applicable due to the inherent dipole imparted on these ring systems.

Key words

azaborines - aromaticity - bicyclic compounds - borazarenes - borazines - boron compounds - cyclization - heterocycles - isosteres
 
  • 1 Bosdet MJD, Piers WE. Can. J. Chem. 2009; 87: 8
  • 2 Baranac-Stojanović M. Chem.–Eur. J. 2014; 20: 16 558
  • 3 Huang J, Li Y. Front. Chem. (Lausanne, Switz.) 2018; 6: 341
  • 4 Giustra ZX, Liu S.-Y. J. Am. Chem. Soc. 2018; 140: 1184
    PubMed
  • 5 Campbell PG, Marwitz AJV, Liu S.-Y. Angew. Chem. Int. Ed. 2012; 51: 6074
    PubMed
  • 6 Wang X.-Y, Wang J.-Y, Pei J. Chem.–Eur. J. 2015; 21: 3528
    PubMed
  • 7 Wang BJ, Groziak MP. Adv. Heterocycl. Chem. 2016; 118: 47
  • 8 Morgan MM, Piers WE. Dalton Trans. 2016; 45: 5920
    PubMed
  • 9 McConnell CR, Liu S.-Y. Chem. Soc. Rev. 2019; 48: 3436
    PubMed
  • 10 Dewar MJS, Marr PA. J. Am. Chem. Soc. 1962; 84: 3782
  • 11 White DG. J. Am. Chem. Soc. 1963; 85: 3634
  • 12 Davies KM, Dewar MJS, Rona P. J. Am. Chem. Soc. 1967; 89: 6294
  • 13 Ashe AJ, Fang X. Org. Lett. 2000; 2: 2089
    PubMed
  • 14 Marwitz AJV, Abbey ER, Jenkins JT, Zakharov LN, Liu S.-Y. Org. Lett. 2007; 9: 4905
    PubMed
  • 15 Marwitz AJV, Matus MH, Zakharov LN, Dixon DA, Liu S.-Y. Angew. Chem. Int. Ed. 2009; 48: 973
    PubMed
  • 16 Abbey ER, Lamm AN, Baggett AW, Zakharov LN, Liu S.-Y. J. Am. Chem. Soc. 2013; 135: 12 908
  • 17 Leonori D, Aggarwal VK. Acc. Chem. Res. 2014; 47: 3174
    PubMed
  • 18 Ashe AJ, Fang X, Fang X, Kampf JW. Organometallics 2001; 20: 5413
  • 19 Pan J, Kampf JW, Ashe AJ. Organometallics 2004; 23: 5626
  • 20 Braunschweig H, Celik MA, Dellermann T, Frenking G, Hammond K, Hupp F, Kelch H, Krummenacher I, Lindl F, Mailänder L, Müssig JH, Ruppert A. Chem.–Eur. J. 2017; 23: 8006
    PubMed
  • 21 Su X, Baker JJ, Martin CD. Chem. Sci. 2020; 11: 126
    PubMed
  • 22 Marwitz AJV, McClintock SP, Zakharov LN, Liu S.-Y. Chem. Commun. (Cambridge) 2010; 46: 779
    PubMed
  • 23 McConnell CR, Campbell PG, Fristoe CR, Memmel P, Zakharov LN, Li B, Darrigan C, Chrostowska A, Liu S.-Y. Eur. J. Inorg. Chem. 2017; 2207
  • 24 Lamm AN, Garner III EB, Dixon DA, Liu S.-Y. Angew. Chem. Int. Ed. 2011; 50: 8157
    PubMed
  • 25 Rudebusch GE, Zakharov LN, Liu S.-Y. Angew. Chem. Int. Ed. 2013; 52: 9316
    PubMed
  • 26 Zhao P, Nettleton DO, Karki RG, Zécri FJ, Liu S.-Y. ChemMedChem 2017; 12: 358
    PubMed
  • 27 Brown AN, Zakharov LN, Mikulas T, Dixon DA, Liu S.-Y. Org. Lett. 2014; 16: 3340
    PubMed
  • 28 Pan J, Kampf JW, Ashe AJ. Org. Lett. 2007; 9: 679
    PubMed
  • 29 Baranac-Stojanović M. J. Org. Chem. 2019; 84: 13 582
  • 30 Zhang Y, Sun F, Dan W, Fang X. J. Org. Chem. 2017; 82: 12 877
  • 31 Zhang Y, Dan W, Fang X. Organometallics 2017; 36: 1677
  • 32 Brown AN, Li B, Liu S.-Y. Tetrahedron 2019; 75: 580
    PubMed
  • 33 Brown AN, Li B, Liu S.-Y. J. Am. Chem. Soc. 2015; 137: 8932
    PubMed
  • 34 Baggett AW, Vasiliu M, Li B, Dixon DA, Liu S.-Y. J. Am. Chem. Soc. 2015; 137: 5536
    PubMed
  • 35 McConnell CR, Haeffner F, Baggett AW, Liu S.-Y. J. Am. Chem. Soc. 2019; 141: 9072
    PubMed
  • 36 Baggett AW, Liu S.-Y. J. Am. Chem. Soc. 2017; 139: 15 259
  • 37 Burford RJ, Li B, Vasiliu M, Dixon DA, Liu S.-Y. Angew. Chem. Int. Ed. 2015; 54: 7823
    PubMed
  • 38 Boger DL. Chem. Rev. 1986; 86: 781
  • 39 García-Rodeja Y, Fernández I. J. Org. Chem. 2016; 81: 6554
    PubMed
  • 40 Edel K, Yang X, Ishibashi JSA, Lamm AN, Maichle-Mössmer C, Giustra ZX, Liu S.-Y, Bettinger HF. Angew. Chem. Int. Ed. 2018; 57: 5296
    PubMed
  • 41 Giustra ZX, Yang X, Chen M, Bettinger HF, Liu S.-Y. Angew. Chem. Int. Ed. 2019; 58: 18 918
  • 42 Baggett AW, Guo F, Li B, Liu S.-Y, Jäkle F. Angew. Chem. Int. Ed. 2015; 54: 11 191
  • 43 Wan W.-M, Baggett AW, Cheng F, Lin H, Liu S.-Y, Jäkle F. Chem. Commun. (Cambridge) 2016; 52: 13 616
  • 44 Xu S, Mikulas TC, Zakharov LN, Dixon DA, Liu S.-Y. Angew. Chem. Int. Ed. 2013; 52: 7527
    PubMed
  • 45 Xu S, Zakharov LN, Liu S.-Y. J. Am. Chem. Soc. 2011; 133: 20 152
  • 46 Li J, Daniliuc CG, Mück-Lichtenfeld C, Kehr G, Erker G. Angew. Chem. Int. Ed. 2019; 58: 15 377
  • 47 Braunschweig H, Damme A, Jimenez-Halla JOC, Pfaffinger B, Radacki K, Wolf J. Angew. Chem. Int. Ed. 2012; 51: 10 034
  • 48 Liu X, Zhang Y, Li B, Zakharov LN, Vasiliu M, Dixon DA, Liu S.-Y. Angew. Chem. Int. Ed. 2016; 55: 8333
    PubMed
  • 49 Liu X, Wu P, Li J, Cui C. J. Org. Chem. 2015; 80: 3737
    PubMed
  • 50 Choi JH, Lim HJ. Org. Biomol. Chem. 2015; 13: 5131
    PubMed
  • 51 de Lescure LR, Jesse T, Groziak MP, Powers XB, Olmstead MM. J. Heterocycl. Chem. 2019; 56: 2960
  • 52 Dewar MJS, Dietz R. J. Chem. Soc. 1959; 2728
  • 53 Paetzold P, Stanescu C, Stubenrauch JR, Bienmüller M, Englert U. Z. Anorg. Allg. Chem. 2004; 630: 2632
  • 54 Wisniewski SR, Guenther CL, Argintaru OA, Molander GA. J. Org. Chem. 2014; 79: 365
    PubMed
  • 55 Davies GHM, Zhou Z.-Z, Jouffroy M, Molander GA. J. Org. Chem. 2017; 82: 549
    PubMed
  • 56 Molander GA, Wisniewski SR, Amani J. Org. Lett. 2014; 16: 5636
    PubMed
  • 57 Paetzold PI, Stohr G, Maisch H, Lenz H. Chem. Ber. 1968; 101: 2881
  • 58 Zhuang F.-D, Han J.-M, Tang S, Yang J.-H, Chen Q.-R, Wang J.-Y, Pei J. Organometallics 2017; 36: 2479
  • 59 Tsuchiya S, Saito H, Nogi K, Yorimitsu H. Org. Lett. 2019; 21: 3855
    PubMed
  • 60 Sargent LJ. J. Org. Chem. 1961; 26: 1754
  • 61 Dewar MJS, Hashmall J, Kubba VP. J. Org. Chem. 1964; 29: 1755
  • 62 Kwong RC, Ma B, Tsai J.-Y, Beers S, Barron E, Kottas G, Dyatkin AB. WO 2010 135 519, 2010
    PubMed
  • 63 Wang X, Davies GHM, Koschitzky A, Wisniewski SR, Kelly CB, Molander GA. Org. Lett. 2019; 21: 2880
    PubMed
  • 64 Dewar MJS, Dietz R. J. Org. Chem. 1961; 26: 3253
  • 65 Molander GA, Wisniewski SR. J. Org. Chem. 2014; 79: 6663
    PubMed
  • 66 Molander GA, Wisniewski SR. J. Org. Chem. 2014; 79: 8339
    PubMed
  • 67 Molander GA, Wisniewski SR, Etemadi-Davan E. J. Org. Chem. 2014; 79: 11 199
  • 68 Davies GHM, Jouffroy M, Sherafat F, Saeednia B, Howshall C, Molander GA. J. Org. Chem. 2017; 82: 8072
    PubMed
  • 69 Compton JS, Saeednia B, Kelly CB, Molander GA. J. Org. Chem. 2018; 83: 9484
    PubMed
  • 70 Molander GA, Wisniewski SR, Traister KM. Org. Lett. 2014; 16: 3692
    PubMed
  • 71 Jouffroy M, Davies GHM, Molander GA. Org. Lett. 2016; 18: 1606
    PubMed
  • 72 Molander GA, Amani J, Wisniewski SR. Org. Lett. 2014; 16: 6024
    PubMed
  • 73 Xu S, Haeffner F, Li B, Zakharov LN, Liu S.-Y. Angew. Chem. Int. Ed. 2014; 53: 6795
    PubMed
  • 74 Chinnapattu M, Sathiyanarayanan KI, Iyer PS. RSC Adv. 2015; 5: 37 716
  • 75 Xu S, Zhang Y, Li B, Liu S.-Y. J. Am. Chem. Soc. 2016; 138: 14 566
  • 76 Liu Z, Ishibashi JSA, Darrigan C, Dargelos A, Chrostowska A, Li B, Vasiliu M, Dixon DA, Liu S.-Y. J. Am. Chem. Soc. 2017; 139: 6082
    PubMed
  • 77 Dewar MJS, Gleicher GJ, Robinson BP. J. Am. Chem. Soc. 1964; 86: 5698
  • 78 Dewar MJS, Jones R. J. Am. Chem. Soc. 1968; 90: 2137
  • 79 Fang X, Yang H, Kampf JW, Banaszak Holl MM, Ashe AJ. Organometallics 2006; 25: 513
  • 80 Sun F, Lv L, Huang M, Zhou Z, Fang X. Org. Lett. 2014; 16: 5024
    PubMed
  • 81 Rohr AD, Kampf JW, Ashe AJ. Organometallics 2014; 33: 1318
  • 82 Abengózar A, Fernández-González MA, Sucunza D, Frutos LM, Salgado A, García-García P, Vaquero JJ. Org. Lett. 2018; 20: 4902
    PubMed
  • 83 Sun F, Huang M, Zhou Z, Fang X. RSC Adv. 2015; 5: 75 607