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Synthesis 2012; 44(8): 1131-1151
DOI: 10.1055/s-0031-1290503
DOI: 10.1055/s-0031-1290503
review
Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives
Weitere Informationen
Publikationsverlauf
Received: 23. Januar 2012
Accepted after revision: 17. Februar 2012
Publikationsdatum:
22. März 2012 (online)
Abstract
Propargylic alcohols are valuable starting materials in organic synthesis; they are easily accessible and can be functionalized further, either through the triple bond or the alcohol functionality. Certain transition metals such as ruthenium or gold have an affinity for propargylic alcohols or alkyne units, which allows for catalytic activation of these substance classes. This review article provides a survey of various transition-metal-catalyzed functionalizations of propargylic alcohols with an emphasis on the latest literature. Examples of nucleophilic propargylic substitution reactions, allene formation, addition and coupling reactions, cyclization reactions, Meyer–Schuster, Rupe and redox–isomerization reactions are given in the article, along with the scope and limitations of the corresponding transformations and mechanistic considerations.
1 Introduction
2 Nucleophilic Propargylic Substitution Reactions
2.1 Nucleophilic Propargylic Substitution Reactions with Propargylic Alcohols
2.2 Nucleophilic Substitution Reactions Employing Propargylic Esters
2.3 Propargylic Amination Reactions
2.4 Mechanisms
3 Allene Formation
4 Addition and Coupling Reactions Involving the Alkyne Unit
5 Cyclization Reactions
5.1 Intramolecular Cycloisomerization or Substitution Reactions
5.2 Intramolecular Cyclization Reactions Preceded by a Propargylic Substitution or Addition Reaction
6 Isomerization Reactions
6.1 Meyer–Schuster Rearrangements
6.2 The Rupe Rearrangement
6.3 Redox Isomerizations
7 Conclusion and Outlook
-
References
- 1 Trost BM, Weiss AH. Adv. Synth. Catal. 2009; 351: 963
- 2 Tlais SF, Clark RJ, Dudley GB. Molecules 2009; 14: 5216
- 3a Ahlsten N, Bartoszewicza A, Martín-Matute B. Dalton Trans. 2012; 41: 1660
- 3b Hartwig JF, Stanley LM. Acc. Chem. Res. 2010; 43: 1461
- 3c Alexakis A, Bäckvall JE, Krause N, Pámies O, Diéguez M. Chem. Rev. 2008; 108: 2796
- 3d Lu Z, Ma S. Angew. Chem. Int. Ed. 2008; 47: 258
- 3e Bruneau C, Renaud J.-L, Demerseman B. Pure Appl. Chem. 2001; 80: 861
- 3f Geurts K, Fletcher SP, van Zijl AW, Minnaard AJ, Feringa BL. Pure Appl. Chem. 2008; 80: 1025
- 4 Cadierno V, Gimeno J. Chem. Rev. 2009; 109: 3512
- 5a Schmidbaur H, Schier A. Organometallics 2010; 29: 2
- 5b de Mendoza P, Echavarren AM. Pure Appl. Chem. 2010; 82: 801
MissingFormLabel
- 5c Xiao J, Li X. Angew. Chem. Int. Ed. 2011; 50: 7226
- 5d Yamamoto Y, Gridnev ID, Patil NT, Jin T. Chem. Commun. 2009; 5075
- 6 Ding C.-H, Hou X.-L. Chem. Rev. 2011; 111: 1914
- 7 Kabalka GW, Yao M.-L. Curr. Org. Synth. 2008; 5: 28
- 8a Nicholas KM, Pettit R. J. Organomet. Chem. 1972; 44: C21
- 8b Nicholas KM. Acc. Chem. Res. 1987; 20: 207
MissingFormLabel
- 8c Teobald BJ. Tetrahedron 2002; 58: 4133
- 9a Djurdjevic S, Yang F, Green JR. J. Org. Chem. 2010; 75: 8241
- 9b Ortega N, Martín VS, Martín T. J. Org. Chem. 2010; 75: 6660
- 9c Green JR, Tjeng AA. J. Org. Chem. 2009; 74: 7411
- 9d Hernández JN, Ramírez MA, Rodríguez ML, Martín VS. Org. Lett. 2008; 10: 2349
- 9e Díaz DD, Betancort JM, Martín VS. Synlett 2007; 343
- 9f Álvaro E, de la Torre MC, Sierra MA. Chem.–Eur. J. 2006; 12: 6403
- 9g Hosokawa S, Isobe M. J. Org. Chem. 1999; 64: 37
- 10 Ljungdahl N, Pera NP, Andersson KH. O, Kann N. Synlett 2008; 394
- 11a Detz RJ, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem. 2009; 6263
- 11b Ljungdahl N, Kann N. Angew. Chem. Int. Ed. 2009; 48: 642
- 11c Miyake Y, Uemura S, Nishibayashi Y. ChemCatChem 2009; 1: 342
- 12a Nishibayashi Y, Milton MD, Inada Y, Yoshikawa M, Wakiji I, Hidai M, Uemura S. Chem.–Eur. J. 2005; 11: 1433
- 12b Nishibayashi Y, Uemura S. Curr. Org. Chem. 2006; 10: 135
- 13 Nishibayashi Y, Wakiji I, Hidai M. J. Am. Chem. Soc. 2000; 122: 11019
MissingFormLabel
- 14a Nishibayashi Y, Wakiji I, Ishii Y, Uemura S, Hidai M. J. Am. Chem. Soc. 2001; 123: 3393
- 14b Nishibayashi Y, Yoshikawa M, Inada Y, Hidai M, Uemura S. J. Am. Chem. Soc. 2002; 124: 11846
- 15a Inada Y, Nishibayashi Y, Uemura S. Angew. Chem. Int. Ed. 2005; 44: 7715
- 15b Kanao K, Miyake Y, Nishibayashi Y. Organometallics 2009; 28: 2920
- 16a Cadierno V, García-Garrido SE, Gimeno J, Nebra N. Inorg. Chim. Acta 2010; 363: 1912
- 16b Cadierno V, Díez J, García-Garrido SE, Gimeno J. Chem. Commun. 2004; 2716
- 17 Zhan Z.-p, Yu J.-l, Liu H.-j, Cui Y.-y, Yang R.-f, Yang W.-z, Li J.-p. J. Org. Chem. 2006; 71: 8298
- 18 Zhan Z.-p, Yang W.-z, Yang R.-f, Yu J.-l, Li J.-p, Liu H.-j. Chem. Commun. 2001; 3352
- 19 Sherry BD, Radosevich AT, Toste FD. J. Am. Chem. Soc. 2003; 125: 6076
- 20 Georgy M, Boucard V, Campagne J.-M. J. Am. Chem. Soc. 2005; 127: 14180
- 21 Nishibayashi Y, Shinoda A, Miyake Y, Matsuzawa H, Sato M. Angew. Chem. Int. Ed. 2006; 45: 4835
- 22 Lutzung MR, Toste FD. J. Am. Chem. Soc. 2003; 125: 15760
- 23 Kuninobu Y, Ishii E, Takai K. Angew. Chem. Int. Ed. 2007; 46: 3296
- 24 Wang T, Chen X.-l, Zhan Z.-p. Org. Lett. 2011; 13: 3324
- 25a Bustelo E, Dixneuf PH. Adv. Synth. Catal. 2007; 349: 933
- 25b Bustelo E, Dixneuf PH. Adv. Synth. Catal. 2005; 347: 393
- 26 Fang P, Hou X.-L. Org. Lett. 2009; 11: 4612
- 27 Matsuda I, Komori K.-i, Itoh K. J. Am. Chem. Soc. 2002; 124: 9072
- 28 Evans PA, Lawler MJ. Angew. Chem. Int. Ed. 2006; 45: 4970
- 29 Kondo T, Kanda Y, Baba A, Fukuda K, Nakamura A, Wada K, Morisaki Y, Mitsudo T.-a. J. Am. Chem. Soc. 2002; 124: 12960
- 30 Farwick A, Helmchen G. Org. Lett. 2010; 1108
- 31a Hoepping A, Johnson KM, George C, Flippen-Anderson J, Kozikowski AP. J. Med. Chem. 2000; 43: 2064
- 31b Miyachi N, Kanda F, Shibasaki M. J. Org. Chem. 1989; 54: 3511
- 32 Lutz JF. Angew. Chem. Int. Ed. 2007; 46: 1018
- 33 Zani L, Bolm C. Chem. Commun. 2006; 4263
- 34 Imada Y, Yuasa M, Nakamura I, Murahashi S.-I. J. Org. Chem. 1994; 59: 2282
- 35a Hattori G, Matsuzawa H, Miyake Y, Nishibayashi Y. Angew. Chem. Int. Ed. 2008; 47: 3781
- 35b Detz RJ, Delville MM. E, Hiemstra H, van Maarseveen JH. Angew. Chem. Int. Ed. 2008; 47: 3777
- 35c Hattori G, Sakata K, Matsuzawa H, Tanabe Y, Miyake Y, Nishibayashi Y. J. Am. Chem. Soc. 2010; 132: 10592
- 36 Detz RJ, Abiri Z, Griel R, Hiemstra H, van Maarseveen JH. Chem.–Eur. J. 2011; 17: 5921
- 37 Widaman AK, Rath NP, Bauer EB. New J. Chem. 2011; 35: 2427
- 38 Nakamura S, Ohara M, Nakamura Y, Shibata N, Toru T. Chem.–Eur. J. 2010; 16: 2360
- 39 Müller TJ. J. Eur. J. Org. Chem. 2001; 2021
- 40 Auger N, Touchard D, Rigaut S, Halet J.-F, Saillard J.-Y. Organometallics 2003; 22: 1638
- 41 Cadierno V, Gamasa MP, Gimeno J, González-Cueva M, Lastra E, Borge J, García-Granda S, Pérez-Carreño E. Organometallics 1996; 15: 2137
- 42a Bolaño T, Castarlenas R, Esteruelas MA, Oñate E. Organometallics 2008; 27: 6367
- 42b Bustelo E, Jiménez-Tenorio M, Mereiter K, Puerta MC, Valerga P. Organometallics 2002; 21: 1903
- 42c Bruce MI, Low PJ, Tieknink ER. T. J. Organomet. Chem. 1999; 572: 3
- 42d Bernad DJ, Esteruelas MA, López AM, Modrego J, Puerta MC, Valerga P. Organometallics 1999; 18: 4995
- 42e Cadierno V, Gamasa MP, Gimeno J, López-González MC, Borge J, García-Granda S. Organometallics 1997; 16: 4453
- 43a Datta S, Chang C.-L, Yeh K.-L, Liu R.-S. J. Am. Chem. Soc. 2003; 125: 9294
- 43b Shen H.-C, Su H.-L, Hsueh Y.-C, Liu R.-S. Organometallics 2004; 23: 4332
- 44 Yua S, Ma S. Chem. Commun. 2011; 47: 5384
- 45 Yoshida M, Gotou T, Ihara M. Tetrahedron Lett. 2004; 45: 5573
- 46a Kalek M, Stawinski J. Adv. Synth. Catal. 2011; 353: 1741
MissingFormLabel
- 46b Kalek M, Johansson T, Jezowska M, Stawinski J. Org. Lett. 2010; 12: 4702
MissingFormLabel
- 47 Vyas DJ, Hazra CK, Oestreich M. Org. Lett. 2011; 13: 4462
- 48 Ohmiya H, Ito H, Sawamura M. Org. Lett. 2009; 11: 5618
- 49a Vlaar T, Ruijter E, Orrua RV. A. Adv. Synth. Catal. 2011; 353: 809
- 49b McGlacken GP, Fairlamb IJ. S. Eur. J. Org. Chem. 2009; 4011
- 49c Plenio H. Angew. Chem. Int. Ed. 2008; 47: 6954
- 50 Cadierno V, Crochet P, García-Garrido SE, Gimeno J. Dalton Trans. 2004; 3635
- 51 Boeck F, Kribber T, Xiao L, Hintermann L. J. Am. Chem. Soc. 2011; 133: 8138
- 52 Villeneuve K, Tam W. Organometallics 2007; 26: 6082
- 53 Mitsudo T.-a, Hori Y, Yamakawa Y, Watanabe Y. J. Org. Chem. 1987; 52: 2230
MissingFormLabel
- 54a Devanne D, Ruppin C, Dixneuf PH. J. Org. Chem. 1988; 53: 925
MissingFormLabel
- 54b Bruneau C, Kabouche Z, Neveux M, Seiller B. Inorg. Chim. Acta 1994; 222: 154
- 54c Darcel C, Bruneau C, Dixneuf PH, Neef G. J. Chem. Soc., Chem. Commun. 1994; 333
- 55 Štĕpniča P, Demel J, Čejka J. J. Mol. Catal. A: Chem. 2004; 224: 161
- 56a Cadierno V, Francos J, Gimeno J. Green Chem. 2010; 12: 135
- 56b Cadierno V, Francos J, Gimeno J. Organometallics 2011; 30: 852
- 57 Präsang C, Bauer EB In Phosphorus Ligands in Asymmetric Catalysis . Vol. 3. Börner A. Wiley-VCH; Weinheim: 2008: 917
- 58 Costin S, Rath NP, Bauer EB. Adv. Synth. Catal. 2008; 350: 2414
- 59 Yi CS, Gao R. Organometallics 2009; 28: 6585
- 60 Hiett NP, Lynam JM, Welby CE, Whitwood AC. J. Organomet. Chem. 2011; 696: 378
- 61a Müller TJ. J. Synthesis 2012; 44: 159
- 61b Schramm OG, Oeser T, Kaiser M, Brun R, Müller TJ. J. Synlett 2008; 359
- 62 Braun RU, Ansorge M, Müller TJ. J. Chem.–Eur. J. 2006; 12: 9081
- 63 Schramm née Dediu OG, Müller TJ. J. Adv. Synth. Catal. 2006; 348: 2565
- 64 Grisé CM, Barriault L. Org. Lett. 2006; 8: 5905
- 65a Suhre MH, Reif M, Kirsch SF. Org. Lett. 2005; 7: 3925
- 65b Menz H, Kirsch SF. Org. Lett. 2006; 8: 4795
- 66a Berger S, Haak E. Tetrahedron Lett. 2010; 51: 6630
- 66b Haak E. Eur. J. Org. Chem. 2008; 788
- 66c Haak E. Eur. J. Org. Chem. 2007; 2815
- 66d Haak E. Synlett 2006; 1847
- 67 Marco-Contelles J, Soriano E. Chem.–Eur. J. 2007; 13: 1350
- 68 Anjum S, Marco-Contelles J. Tetrahedron 2005; 61: 4793
- 69 Fürstner A, Hannen P. Chem. Commun. 2004; 2546
- 70 Wang Y.-M, Kuzniewski CN, Rauniyar V, Hoong C, Toste FD. J. Am. Chem. Soc. 2011; 133: 12972
- 71 Yamazaki S. Chem.–Eur. J. 2008; 14: 6026
- 72 Cai S, Lui Z, Zhang W, Zhao X, Wang DZ. Angew. Chem. Int. Ed. 2011; 50: 11133
- 73 Debleds O, Gayon E, Ostaszuk E, Vrancken E, Campagne J.-M. Chem.–Eur. J. 2010; 16: 12207
- 74 Gao X, Pan Y.-m, Lin M, Chen L, Zhan Z.-p. Org. Biomol. Chem. 2010; 8: 3259
- 75 Feng X, Tan Z, Chen D, Shen Y, Guo C.-C, Xiang J, Zhu C. Tetrahedron Lett. 2008; 49: 4110
- 76a Cadierno V, Gimeno J, Nebra N. Adv. Synth. Catal. 2007; 349: 382
- 76b Cadierno V, Díez J, Gimeno J, Nebra N. J. Org. Chem. 2008; 73: 5852
- 77 Chen Z, Zhang Y.-X, Wang Y.-H, Zhu LL, Liu H, Li X.-X, Guo L. Org. Lett. 2010; 12: 3468
- 78 Harschneck T, Kirsch SF. J. Org. Chem. 2011; 76: 2145
MissingFormLabel
- 79 Kim I, Kim K. Org. Lett. 2010; 12: 2500
- 80 Guo L.-N, Duan X.-H, Liang Y.-M. Acc. Chem. Res. 2011; 44: 111
- 81a Duan X.-H, Guo L.-N, Bi H.-P, Liu X.-Y, Liang Y.-M. Org. Lett. 2006; 8: 5777
- 81b Bi H.-P, Guo L.-N, Gou F.-R, Duan X.-H, Liu X.-Y, Liang Y.-M. J. Org. Chem. 2008; 73: 4713
- 82a Yoshida M, Sugimura C, Shishido K. Org. Lett. 2011; 13: 3482
- 82b Yoshida M, Higuchi M, Shishido K. Tetrahedron 2010; 66: 2675
- 83 Liu X.-t, Huang L, Zheng F.-j, Zhan Z.-p. Adv. Synth. Catal. 2008; 350: 2778
- 84a Cadierno V, Gimeno J, Nebra N. Chem.–Eur. J. 2007; 13: 9973
- 84b Cadierno V, Gimeno J, Nebra N. J. Heterocycl. Chem. 2010; 47: 233
- 85a Engel DA, Dudley GB. Org. Biomol. Chem. 2009; 7: 4149
- 85b Cadierno V, Crochet P, Gimeno J. Synlett 2008; 1105
- 85c Cadierno V, Crochet P, García-Garrido SE, Gimeno J. Dalton Trans. 2010; 39: 4015
- 86 Picquet M, Bruneau C, Dixneuf PH. Chem. Commun. 1997; 1201
- 87 Cadierno V, García-Garrido SE, Gimeno J. Adv. Synth. Catal. 2006; 348: 101
- 88 Egi M, Umemura M, Kawai T, Akai S. Angew. Chem. Int. Ed. 2011; 50: 12197
- 89 Engel DA, Dudley GB. Org. Lett. 2006; 8: 4027
- 90 Engel DA, Lopez SS, Dudley GB. Tetrahedron 2008; 64: 6988
- 91 Lopez S, Engel DA, Dudley GB. Synlett 2007; 949
- 92 Pennell MN, Unthank MG, Turner P, Sheppard TD. J. Org. Chem. 2011; 76: 1479
- 93 Wang D, Zhang Y, Harris A, Gautam LN. S, Chen Y, Shi X. Adv. Synth. Catal. 2011; 353: 2584
- 94 El Douhaibi AS, Judeh ZM. A, Basri H, Moussa Z, Messali M, Qi G. Synth. Commun. 2011; 41: 533
- 95 Stefanoni M, Luparia M, Porta A, Zanoni G, Vidari G. Chem.–Eur. J. 2009; 15: 3940
- 96 Cadierno V, Francos J, Gimeno J. Tetrahedron Lett. 2009; 50: 4773
- 97 Antiñolo A, Carrillo-Hermosilla F, Cadierno V, García-Álvarez J, Otero A. ChemCatChem 2012; 4: 123
- 98 Parés A, Alibés R, Figueredo M, Font J, Parella T. Eur. J. Org. Chem. 2012; in press; DOI 10.1002/ejoc.201101614
- 99a Onodera G, Matsumoto H, Nishibayashi Y, Uemura S. Organometallics 2005; 24: 5799
- 99b Cadierno V, Díez J, García-Garrido SE, Gimeno J, Nebra N. Adv. Synth. Catal. 2006; 348: 2125
- 100 Bhuvaneswari S, Jeganmohan M, Cheng C.-H. Chem.–Asian J. 2010; 5: 141
- 101 Nolin KA, Ahn RW, Kobayashi Y, Kennedy-Smith JJ, Toste FD. Chem.–Eur. J. 2010; 16: 9555
- 102 Hodgson DM, Talbot EP. A, Clark BP. Org. Lett. 2011; 13: 5751
- 103 Egi M, Yamaguchi Y, Fujiwara N, Akai S. Org. Lett. 2008; 10: 1867
- 104 Borge J, Cadierno V, Díez J, García-Garrido SE, Gimeno J. Dyes Pigm. 2010; 87: 209
- 105 Cadierno V, Gimeno J, Nebra N. ChemCatChem 2010; 5: 519
- 106 Trost BM, Livingston RC. J. Am. Chem. Soc. 1995; 117: 9586
- 107 Tanaka K, Shoji T, Hirano M. Eur. J. Org. Chem. 2007; 2687
- 108 Trost BM, Breder A. Org. Lett. 2011; 13: 398