Yu, J.-Q.: 2015 Science of Synthesis, 3b: Catalytic Transformations via C-H Activation 2 DOI: 10.1055/sos-SD-218-00001
Catalytic Transformations via C—H Activation 2

2.1 C—C and C—X Bond Formation by Allylic C—H Activation

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Book

Editor: Yu, J.-Q.

Authors: Carreira, E. M.; Decicco, C. P.; Fuerstner, A.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Title: Catalytic Transformations via C-H Activation 2

Print ISBN: 9783132057210; Online ISBN: 9783132404137; Book DOI: 10.1055/b-004-129675

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

 


Abstract

This chapter documents recent studies into allylic functionalization via C—H activation processes catalyzed by metals such as palladium, rhodium, ruthenium, copper, and iron. The focus is on the formation of C—C, C—N, and C—O bonds reported in the last two decades, but more recent developments involving the formation of other C—X bonds, such as C—F and C—Si are also highlighted.

 
  • 1 Topics in Current Chemistry. Yu J.-Q, Shi Z. Springer; Heidelberg 2010. 292.
  • 2 Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
  • 3 Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
  • 4 Newhouse T, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362
  • 5 Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
  • 6 Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
  • 7 Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
  • 8 McMurray L, OʼHara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
  • 9 Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E. Wiley; New York 2002
  • 10 Li H, Li B.-J, Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
  • 11 Andrus MB, Lashley JC. Tetrahedron 2002; 58: 845
  • 12 Eames J, Watkinson M. Angew. Chem. Int. Ed. 2001; 40: 3567
  • 13 Hüttel R, Christ H. Chem. Ber. 1963; 96: 3101
  • 14 Engelin CJ, Fristrup P. Molecules 2011; 16: 951
  • 15 Chrisope DR, Beak P. J. Am. Chem. Soc. 1986; 108: 334
  • 16 Chrisope DR, Beak P, Saunders WH. J. Am. Chem. Soc. 1988; 110: 230
  • 17 Engelin C, Jensen T, Rodriguez-Rodriguez S, Fristrup P. ACS Catal. 2013; 3: 294
  • 18 Tsuji J, Takahashi H, Morikawa M. Tetrahedron Lett. 1965; 6: 4387
  • 19 Trost BM. Acc. Chem. Res. 1980; 13: 385
  • 20 Trost BM, Fullerton TJ. J. Am. Chem. Soc. 1973; 95: 292
  • 21 Trost BM, Weber L, Strege PE, Fullerton TJ, Dietsche TJ. J. Am. Chem. Soc. 1978; 100: 3416
  • 22 Trost BM, Metzner PJ. J. Am. Chem. Soc. 1980; 102: 3572
  • 23 Lin S, Song C.-X, Cai G.-X, Wang W.-H, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 12901
  • 24 Young AJ, White MC. J. Am. Chem. Soc. 2008; 130: 14090
  • 25 Young AJ, White MC. Angew. Chem. Int. Ed. 2011; 50: 6824
  • 26 Trost BM, Hansmann MM, Thaisrivongs DA. Angew. Chem. Int. Ed. 2012; 51: 4950
  • 27 Li L, Chen Q.-Y, Guo Y. Chem. Commun. (Cambridge) 2013; 49: 8764
  • 28 Chen H, Cai C, Liu X, Li X, Jiang H. Chem. Commun. (Cambridge) 2011; 47: 12224
  • 29 Aydin J, Szabó KJ. Org. Lett. 2008; 10: 2881
  • 30 Chai Z, Rainey TJ. J. Am. Chem. Soc. 2012; 134: 3615
  • 31 Trost BM, Thaisrivongs DA, Donckele EJ. Angew. Chem. Int. Ed. 2013; 52: 1523
  • 32 Aubert C, Buisine O, Malacria M. Chem. Rev. 2002; 102: 813
  • 33 Michelet V, Toullec PY, Genêt J.-P. Angew. Chem. Int. Ed. 2008; 47: 4268
  • 34 Brummond KM, Chen H, Mitasev B, Casarez AD. Org. Lett. 2004; 6: 2161
  • 35 Li W, Yuan W, Shi M, Hernandez E, Li G. Org. Lett. 2010; 12: 64
  • 36 Li Q, Yu Z.-X. J. Am. Chem. Soc. 2010; 132: 4542
  • 37 Li Q, Yu Z.-X. Organometallics 2012; 31: 5185
  • 38 Li Q, Yu Z.-X. Angew. Chem. Int. Ed. 2011; 50: 2144
  • 39 Trost BM, Toste FD. J. Am. Chem. Soc. 1999; 121: 9728
  • 40 Trost BM, Surivet J.-P, Toste FD. J. Am. Chem. Soc. 2004; 126: 15592
  • 41 Trost BM, Toste FD. J. Am. Chem. Soc. 2002; 124: 5025
  • 42 Trost BM, Gutierrez AC, Ferreira EM. J. Am. Chem. Soc. 2010; 132: 9206
  • 43 Ajamian A, Gleason JL. Org. Lett. 2003; 5: 2409
  • 44 Rakshit S, Patureau FW, Glorius F. J. Am. Chem. Soc. 2010; 132: 9585
  • 45 Li C.-J. Acc. Chem. Res. 2009; 42: 335
  • 46 Yoo W.-J, Li C.-J. Top. Curr. Chem. 2010; 292: 281
  • 47 Li Z, Li C.-J. J. Am. Chem. Soc. 2006; 128: 56
  • 48 Xu J, Fu Y, Luo D.-F, Jiang Y.-Y, Xiao B, Liu Z.-J, Gong T.-J, Liu L. J. Am. Chem. Soc. 2011; 133: 15300
  • 49 Parsons AT, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 9120
  • 50 Wang X, Ye Y, Zhang S, Feng J, Xu Y, Zhang Y, Wang J. J. Am. Chem. Soc. 2011; 133: 16410
  • 51 Chu L, Qing F.-L. Org. Lett. 2012; 14: 2106
  • 52 Liu H, Cao L, Sun J, Fossey JS, Deng W.-P. Chem. Commun. (Cambridge) 2012; 48: 2674
  • 53 Sekine M, Ilies L, Nakamura E. Org. Lett. 2013; 15: 714
  • 54 Wolff ME. Chem. Rev. 1963; 63: 55
  • 55 Moody CJ, Comprehensive Organic Synthesis. Trost BM, Fleming I. Pergamon; Oxford 1991. 7.
  • 56 Åkermark B, Åkermark G, Hegedus LS, Zetterberg K. J. Am. Chem. Soc. 1981; 103: 3037
  • 57 van der Schaaf PA, Sutter J.-P, Grellier M, van Mier GPM, Spek AL, van Koten G, Pfeffer M. J. Am. Chem. Soc. 1994; 116: 5134
  • 58 Larock RC, Hightower TR, Hasvold LA, Hasvold LA, Peterson KP. J. Org. Chem. 1996; 61: 3584
  • 59 Fraunhoffer KJ, White MC. J. Am. Chem. Soc. 2007; 129: 7274
  • 60 Jiang C, Covell DJ, Stepan AF, Plummer MS, White MC. Org. Lett. 2012; 14: 1386
  • 61 Rice GT, White MC. J. Am. Chem. Soc. 2009; 131: 11707
  • 62 Strambeanu II, White MC. J. Am. Chem. Soc. 2013; 135: 12032
  • 63 Wu L, Qiu S, Liu G. Org. Lett. 2009; 11: 2707
  • 64 Reed SA, White MC. J. Am. Chem. Soc. 2008; 130: 3316
  • 65 Reed SA, Mazzotti AR, White MC. J. Am. Chem. Soc. 2009; 131: 11701
  • 66 Liu G, Yin G, Wu L. Angew. Chem. Int. Ed. 2008; 47: 4733
  • 67 Yin G, Wu Y, Liu G. J. Am. Chem. Soc. 2010; 132: 11978
  • 68 Shimizu Y, Obora Y, Ishii Y. Org. Lett. 2010; 12: 1372
  • 69 Du H, Yuan W, Zhao B, Shi Y. J. Am. Chem. Soc. 2007; 129: 7496
  • 70 Du H, Zhao B, Shi Y. J. Am. Chem. Soc. 2008; 130: 8590
  • 71 Wang B, Du H, Shi Y. Angew. Chem. Int. Ed. 2008; 47: 8224
  • 72 Luzung MR, Lewis CA, Baran PS. Angew. Chem. Int. Ed. 2009; 48: 7025
  • 73 Xiong T, Li Y, Mao L, Zhang Q, Zhang Q. Chem. Commun. (Cambridge) 2012; 48: 2246
  • 74 Zalatan DN, Du Bois J. Top. Curr. Chem. 2010; 292: 347
  • 75 Dequirez G, Pons V, Dauban P. Angew. Chem. Int. Ed. 2012; 51: 7384
  • 76 Roizen JL, Harvey ME, Du Bois J. Acc. Chem. Res. 2012; 45: 911
  • 77 Du Bois J. Org. Process Res. Dev. 2011; 15: 758
  • 78 Espino CG, Wehn PM, Chow J, Du Bois J. J. Am. Chem. Soc. 2001; 123: 6935
  • 79 Yu X.-Q, Huang J.-S, Zhou X.-G, Che C.-M. Org. Lett. 2000; 2: 2233
  • 80 Liang J.-L, Yuan S.-X, Chan PWH, Che C.-M. Org. Lett. 2002; 4: 4507
  • 81 Lebel H, Huard K, Lectard S. J. Am. Chem. Soc. 2005; 127: 14198
  • 82 Parker KA, Chang W. Org. Lett. 2005; 7: 1785
  • 83 Zalatan DN, Du Bois J. J. Am. Chem. Soc. 2008; 130: 9220
  • 84 Harvey ME, Musaev DG, Du Bois J. J. Am. Chem. Soc. 2011; 133: 17207
  • 85 Cochet T, Bellosta V, Roche D, Ortholand J.-Y, Greiner A, Cossy J. Chem. Commun. (Cambridge) 2012; 48: 10745
  • 86 Lebel H, Spitz C, Leogane O, Trudel C, Parmentier M. Org. Lett. 2011; 13: 5460
  • 87 Liang C, Collet F, Robert-Peillard F, Müller P, Dodd RH, Dauban P. J. Am. Chem. Soc. 2008; 130: 343
  • 88 Lescot C, Darses B, Collet F, Retailleau P, Dauban P. J. Org. Chem. 2012; 77: 7232
  • 89 Liang J.-L, Yuan S.-X, Huang J.-S, Che C.-M. J. Org. Chem. 2004; 69: 3610
  • 90 Dauban P, Dodd RH. Org. Lett. 2000; 2: 2327
  • 91 Dauban P, Sanière L, Tarrade A, Dodd RH. J. Am. Chem. Soc. 2001; 123: 7707
  • 92 Milczek E, Boudet N, Blakey S. Angew. Chem. Int. Ed. 2008; 47: 6825
  • 93 Nishioka Y, Uchida T, Katsuki T. Angew. Chem. Int. Ed. 2013; 52: 1739
  • 94 Breslow R, Gellman SH. J. Chem. Soc., Chem. Commun. 1982; 1400
  • 95 Albone DP, Aujla PS, Taylor PC. J. Org. Chem. 1998; 63: 9569
  • 96 Bhuyan R, Nicholas KM. Org. Lett. 2007; 9: 3957
  • 97 Paradine SM, White MC. J. Am. Chem. Soc. 2012; 134: 2036
  • 98 Hennessy ET, Betley TA. Science (Washington, D. C.) 2013; 340: 591
  • 99 Lu H, Jiang H, Hu Y, Wojtas L, Zhang XP. Chem. Sci. 2011; 2: 2361
  • 100 Kohmura Y, Kawasaki K, Katsuki T. Synlett 1997; 1456
  • 101 Clark JS, Roche C. Chem. Commun. (Cambridge) 2005; 5175
  • 102 Smith K, Hupp CD, Allen KL, Slough GA. Organometallics 2005; 24: 1747
  • 103 Pelletier G, Powell DA. Org. Lett. 2006; 8: 6031
  • 104 Gephart III RT, Huang DL, Aguila MJB, Schmidt G, Shahu A, Warren TH. Angew. Chem. Int. Ed. 2012; 51: 6488
  • 105 Qin C, Jiao N. J. Am. Chem. Soc. 2010; 132: 15893
  • 106 Srivastava RS, Nicholas KM. J. Am. Chem. Soc. 1997; 119: 3302
  • 107 Lumbroso A, Cooke ML, Breit B. Angew. Chem. Int. Ed. 2013; 52: 1890
  • 108 Green M, Haszeldine RN, Lindley J. J. Organomet. Chem. 1966; 6: 107
  • 109 McMurry JE, Kočovský P. Tetrahedron Lett. 1984; 25: 4187
  • 110 Heumann A, Åkermark B. Angew. Chem. Int. Ed. Engl. 1984; 23: 453
  • 111 Hansson S, Heumann A, Rein T, Åkermark B. J. Org. Chem. 1990; 55: 975
  • 112 Byström SE, Larsson EM, Åkermark B. J. Org. Chem. 1990; 55: 5674
  • 113 Bäckvall J.-E, Hopkins RB, Grennberg H, Mader MM, Awasthi AK. J. Am. Chem. Soc. 1990; 112: 5160
  • 114 Åkermark B, Larsson EM, Oslob JD. J. Org. Chem. 1994; 59: 5729
  • 115 Kitching W, Rappoport Z, Winstein S, Young WG. J. Am. Chem. Soc. 1966; 88: 2054
  • 116 Chen MS, White MC. J. Am. Chem. Soc. 2004; 126: 1346
  • 117 Vermeulen NA, Delcamp JH, White MC. J. Am. Chem. Soc. 2010; 132: 11323
  • 118 Thiery E, Aouf C, Belloy J, Harakat D, Le Bras J, Muzart J. J. Org. Chem. 2010; 75: 1771
  • 119 Chen MS, Prabagaran N, Labenz NA, White MC. J. Am. Chem. Soc. 2005; 127: 6970
  • 120 Fraunhoffer KJ, Prabagaran N, Sirois LE, White MC. J. Am. Chem. Soc. 2006; 128: 9032
  • 121 Stang EM, White MC. Angew. Chem. Int. Ed. 2011; 50: 2094
  • 122 Gormisky PE, White MC. J. Am. Chem. Soc. 2011; 133: 12584
  • 123 Pilarski LT, Selander N, Böse D, Szabó KJ. Org. Lett. 2009; 11: 5518
  • 124 Lin B.-L, Labinger JA, Bercaw JE. Can. J. Chem. 2009; 87: 264
  • 125 Campbell AN, White PB, Guzei IA, Stahl SS. J. Am. Chem. Soc. 2010; 132: 15116
  • 126 Henderson WH, Check CT, Proust N, Stambuli JP. Org. Lett. 2010; 12: 824
  • 127 Le C, Kunchithapatham K, Henderson WH, Check CT, Stambuli JP. Chem.–Eur. J. 2013; 19: 11153
  • 128 Mitsudome T, Umetani T, Nosaka N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Angew. Chem. Int. Ed. 2006; 45: 481
  • 129 Pilarski LT, Janson PG, Szabó KJ. J. Org. Chem. 2010; 76: 1503
  • 130 Alam R, Pilarski LT, Pershagen E, Szabó KJ. J. Am. Chem. Soc. 2012; 134: 8778
  • 131 Check CT, Henderson WH, Wray BC, Vanden Eynden MJ, Stambuli JP. J. Am. Chem. Soc. 2011; 133: 18503
  • 132 Chen H, Jiang H, Cai C, Dong J, Fu W. Org. Lett. 2011; 13: 992
  • 133 Covell DJ, White MC. Angew. Chem. Int. Ed. 2008; 47: 6448
  • 134 Takenaka K, Akita M, Tanigaki Y, Takizawa S, Sasai H. Org. Lett. 2011; 13: 3506
  • 135 Kharasch MS, Sosnovsky G. J. Am. Chem. Soc. 1958; 80: 756
  • 136 Kharasch MS, Sosnovsky G, Yang NC. J. Am. Chem. Soc. 1959; 81: 5819
  • 137 Walling C, Zavitsas AA. J. Am. Chem. Soc. 1963; 85: 2084
  • 138 Beckwith ALJ, Zavitsas AA. J. Am. Chem. Soc. 1986; 108: 8230
  • 139 Andrus MB, Zhou Z. J. Am. Chem. Soc. 2002; 124: 8806
  • 140 Zhou Z, Andrus MB. Tetrahedron Lett. 2012; 53: 4518
  • 141 Gokhale AS, Minidis ABE, Pfaltz A. Tetrahedron Lett. 1995; 36: 1831
  • 142 Sekar G, DattaGupta A, Singh VK. J. Org. Chem. 1998; 63: 2961
  • 143 Ginotra SK, Singh VK. Org. Biomol. Chem. 2006; 4: 4370
  • 144 Andrus MB, Asgari D. Tetrahedron 2000; 56: 5775
  • 145 Kawasaki K, Katsuki T. Tetrahedron 1997; 53: 6337
  • 146 Zondervan C, Feringa BL. Tetrahedron: Asymmetry 1996; 7: 1895
  • 147 Södergren MJ, Andersson PG. Tetrahedron Lett. 1996; 37: 7577
  • 148 Teng P.-F, Tsang C.-S, Yeung H.-L, Wong W.-L, Kwong H.-L, Williams ID. J. Organomet. Chem. 2006; 691: 2237
  • 149 Malkov AV, Bella M, Langer V, Kočovský P. Org. Lett. 2000; 2: 3047
  • 150 Hoang VDM, Reddy PAN, Kim T.-J. Organometallics 2008; 27: 1026
  • 151 Zhang B, Zhu S.-F, Zhou Q.-L. Tetrahedron Lett. 2013; 54: 2665
  • 152 Wang T, Xiang S.-K, Qin C, Ma J.-A, Zhang L.-H, Jiao N. Tetrahedron Lett. 2011; 52: 3208
  • 153 Larsson JM, Zhao TSN, Szabó KJ. Org. Lett. 2011; 13: 1888
  • 154 Braun M.-G, Doyle AG. J. Am. Chem. Soc. 2013; 135: 12990