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Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00113
Multicomponent Reactions, Volume 2

2.3 Boron-Mediated Multicomponent Reactions

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Book

Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

Title: Multicomponent Reactions, Volume 2

Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions

Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Multicomponent Reactions

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

Organoboronates are important reagents in modern synthetic applications. However, some organoboronates are unstable or difficult to purify. A possible solution is to perform organic transformations with in situ generated organoboronates. The organoboronates react selectively with many substrates, such as carbonyl compounds (allylation reactions) or organohalides (Suzuki–Miyaura coupling). Furthermore, synthesis of organoboronates and the subsequent transformations can be easily combined in the same reaction vessel. This chapter presents examples of these reactions including generation of organoboronates from simple prefunctionalized substrates (such as alcohols) and via C—H functionalization processes.

Key words

homogeneous catalysis - C—B bond formation - allylation - Suzuki–Miyaura coupling - selectivity
 
  • 1 Hall DG. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. Wiley-VCH; Weinheim, Germany 2011
    Google Scholar
  • 2 Hartwig JF. Organotransition Metal Chemistry. University Science Books; Sausalito, CA 2010
    Google Scholar
  • 3 Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. Wiley; Chichester, UK 2004
    Google Scholar
  • 4 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
  • 5 Kündig P. Science (Washington, D. C.) 2006; 314: 430
  • 6 Kennedy JWJ, Hall DG. Angew. Chem. Int. Ed. 2003; 42: 4732
  • 7 Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
  • 8 Hoffmann RW. Angew. Chem. Int. Ed. Engl. 1982; 21: 555
  • 9 Hall DG. Synlett 2007; 1644
  • 10 Qiao JX, Lam PYS. Synthesis 2011; 829
  • 11 Tzschucke CC, Murphy JM, Hartwig JF. Org. Lett. 2007; 9: 761
  • 12 Maleczka Jr RE, Shi F, Holmes D, Smith III MR. J. Am. Chem. Soc. 2003; 125: 7792
  • 13 Raducan M, Alam R, Szabó KJ. Angew. Chem. Int. Ed. 2012; 51: 13050
  • 14 Braverman S, Pechenick T, Zafrani Y. ARKIVOC 2004; 51
  • 15 Snyder HR, Kuck JA, Johnson JR. J. Am. Chem. Soc. 1938; 60: 105
  • 16 Brown HC, Racherla US, Pellechia PJ. J. Org. Chem. 1990; 55: 1868
  • 17 Selander N, Kipke A, Sebelius S, Szabó KJ. J. Am. Chem. Soc. 2007; 129: 13723
  • 18 Selander N, Sebelius S, Estay C, Szabó KJ. Eur. J. Org. Chem. 2006; 4085
  • 19 Selander N, Paasch JR, Szabó KJ. J. Am. Chem. Soc. 2011; 133: 409
  • 20 Sebelius S, Wallner OA, Szabó KJ. Org. Lett. 2003; 5: 3065
  • 21 Tailor J, Hall DG. Org. Lett. 2000; 2: 3715
  • 22 Touré BB, Hoveyda HR, Tailor J, Ulaczyk-Lesanko A, Hall DG. Chem.–Eur. J. 2003; 9: 466
  • 23 Rauniyar V, Hall DG. J. Am. Chem. Soc. 2004; 126: 4518
  • 24 Ishiyama T, Ahiko T.-a, Miyaura N. J. Am. Chem. Soc. 2002; 124: 12414
  • 25 Sakata K, Fujimoto H. J. Am. Chem. Soc. 2008; 130: 12519
  • 26 Wang H, Jain P, Antilla JC, Houk KN. J. Org. Chem. 2013; 78: 1208
  • 27 Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
  • 28 Larsson JM, Szabó KJ. J. Am. Chem. Soc. 2013; 135: 443
  • 29 Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
  • 30 Miyaura N. Top. Curr. Chem. 2002; 219: 11
  • 31 Saito B, Fu GC. J. Am. Chem. Soc. 2007; 129: 9602
  • 32 Lu Z, Fu GC. Angew. Chem. Int. Ed. 2010; 49: 6676
  • 33 Saito B, Fu GC. J. Am. Chem. Soc. 2008; 130: 6694
  • 34 Omoto K, Fujimoto H. J. Org. Chem. 1998; 63: 8331
  • 35 Schneider U, Kobayashi S. Angew. Chem. Int. Ed. 2007; 46: 5909
  • 36 Schneider U, Ueno M, Kobayashi S. J. Am. Chem. Soc. 2008; 130: 13824
  • 37 Lou S, Moquist PN, Schaus SE. J. Am. Chem. Soc. 2006; 128: 12660
  • 38 Wada R, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2004; 126: 8910
  • 39 Selander N, Szabó KJ. Adv. Synth. Catal. 2008; 350: 2045
  • 40 Kabalka GW, Venkataiah B, Dong G. Tetrahedron Lett. 2005; 46: 4209
  • 41 Ishiyama T, Ahiko T.-a, Miyaura N. Tetrahedron Lett. 1996; 37: 6889
  • 42 Ito H, Okura T, Matsuura K, Sawamura M. Angew. Chem. Int. Ed. 2010; 49: 560
  • 43 Ito H, Kawakami C, Sawamura M. J. Am. Chem. Soc. 2005; 127: 16034
  • 44 Ito H, Ito S, Sasaki Y, Matsuura K, Sawamura M. J. Am. Chem. Soc. 2007; 129: 14856
  • 45 Lessard S, Peng F, Hall DG. J. Am. Chem. Soc. 2009; 131: 9612
  • 46 Hall DG, Ding J. Angew. Chem. Int. Ed. 2013; 52: 8069
  • 47 Murata M, Oyama T, Watanabe S, Masuda Y. Synthesis 2000; 778
  • 48 Selander N, Szabó KJ. Chem. Commun. (Cambridge) 2008; 3420
  • 49 Sebelius S, Olsson VJ, Wallner OA, Szabó KJ. J. Am. Chem. Soc. 2006; 128: 8150
  • 50 Petasis NA, Zavialov IA. J. Am. Chem. Soc. 1997; 119: 445
  • 51 Petasis NA, Zavialov IA. J. Am. Chem. Soc. 1998; 120: 11798
  • 52 Candeias NR, Montalbano F, Cal PMSD, Gois PMP. Chem. Rev. 2010; 110: 6169
  • 53 Selander N, Szabó KJ, Asymmetric Synthesis and Application of α-Amino Acids. Soloshonok VA, Izawa K. American Chemical Society; Washington, DC 2009
    Google Scholar
  • 54 Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
  • 55 Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
  • 56 Randl S, Connon SJ, Blechert S. Chem. Commun. (Cambridge) 2001; 1796
  • 57 Schlosser M, Stähle M. Angew. Chem. Int. Ed. Engl. 1980; 19: 487
  • 58 Kennedy JWJ, Hall DG. J. Am. Chem. Soc. 2002; 124: 11586
  • 59 Alam R, Raducan M, Eriksson L, Szabó KJ. Org. Lett. 2013; 15: 2546
  • 60 Yamamoto Y, Takada S, Miyaura N. Chem. Lett. 2006; 35: 704
  • 61 Yamamoto Y, Takada S, Miyaura N. Organometallics 2009; 28: 152
  • 62 Glasspoole BW, Ghozati K, Moir JW, Crudden CM. Chem. Commun. (Cambridge) 2012; 48: 1230
  • 63 Farmer JL, Hunter HN, Organ MG. J. Am. Chem. Soc. 2012; 134: 17470
  • 64 Vougioukalakis GC, Grubbs RH. Chem. Rev. 2009; 110: 1746
  • 65 Grubbs RH, Chang S. Tetrahedron 1998; 54: 4413
  • 66 Goldberg SD, Grubbs RH. Angew. Chem. Int. Ed. 2002; 41: 807
  • 67 Jernelius JA, Schrock RR, Hoveyda AH. Tetrahedron 2004; 60: 7345
  • 68 Hartwig JF. Acc. Chem. Res. 2012; 45: 864
  • 69 Olsson VJ, Szabó KJ. Angew. Chem. Int. Ed. 2007; 46: 6891
  • 70 Olsson VJ, Szabó KJ. J. Org. Chem. 2009; 74: 7715
  • 71 Caballero A, Sabo-Etienne S. Organometallics 2007; 26: 1191
  • 72 Selander N, Willy B, Szabó KJ. Angew. Chem. Int. Ed. 2010; 49: 4051
  • 73 Olsson VJ, Szabó KJ. Org. Lett. 2008; 10: 3129
  • 74 Gao X, Hall DG. J. Am. Chem. Soc. 2003; 125: 9308
  • 75 Touré BB, Hall DG. Angew. Chem. Int. Ed. 2004; 43: 2001
  • 76 Gao X, Hall DG, Deligny M, Favre A, Carreaux F, Carboni B. Chem.–Eur. J. 2006; 12: 3132
  • 77 Gademann K, Chavez DE, Jacobsen EN. Angew. Chem. Int. Ed. 2002; 41: 3059
  • 78 Cho J.-Y, Tse MK, Holmes D, Maleczka Jr RE, Smith III MR. Science (Washington, D. C.) 2002; 295: 305
  • 79 Kikuchi T, Nobuta Y, Umeda J, Yamamoto Y, Ishiyama T, Miyaura N. Tetrahedron 2008; 64: 4967
  • 80 Vanchura II BA, Preshlock SM, Roosen PC, Kallepalli VA, Staples RJ, Maleczka Jr RE, Singleton DA, Smith M. R., III. Chem. Commun. (Cambridge) 2010; 46: 7724
  • 81 Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992
  • 82 Harrisson P, Morris J, Steel PG, Marder TB. Synlett 2009; 147
  • 83 Beck EM, Hatley R, Gaunt MJ. Angew. Chem. Int. Ed. 2008; 47: 3004
  • 84 Norberg AM, Smith III MR, Maleczka Jr RE. Synthesis 2011; 857
  • 85 Murphy JM, Liao X, Hartwig JF. J. Am. Chem. Soc. 2007; 129: 15434
  • 86 Liskey CW, Liao X, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 11389
  • 87 Molander GA, Trice SLJ, Dreher SD. J. Am. Chem. Soc. 2010; 132: 17701
  • 88 Molander GA, Trice SLJ, Kennedy SM, Dreher SD, Tudge MT. J. Am. Chem. Soc. 2012; 134: 11667
  • 89 Billingsley KL, Barder TE, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 5359
  • 90 Tasch BOA, Merkul E, Müller TJJ. Eur. J. Org. Chem. 2011; 4532
  • 91 Tasch BOA, Antovic D, Merkul E, Müller TJJ. Eur. J. Org. Chem. 2013; 4564
  • 92 Pilarski LT, Szabó KJ. Angew. Chem. Int. Ed. 2011; 50: 8230