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DOI: 10.1055/s-0034-1378852
Coinage-Metal-Catalyzed Reactions of Propargylic Alcohols
Publikationsverlauf
Received: 11. Dezember 2014
Accepted after revision: 24. April 2015
Publikationsdatum:
04. August 2015 (online)
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Abstract
Propargylic alcohols, which possess inherent alkynyl and hydroxyl functional groups, are one of the most valuable bifunctional building blocks in the field of organic synthesis. The simple generation and conversion of these compounds into various valuable products make propargylic alcohols a powerful tool for synthetic organic chemists. These conversions have been largely achieved using transition-metal-catalytic systems, especially those using coinage metals (i.e., copper, silver and gold). However, few reviews focusing on these transformations have been published. This review summarizes the chemistry of propargylic alcohol moiety based reactions controlled by coinage-metal-catalytic systems.
1 Introduction
2 Nucleophilic Substitution Reactions
3 Rearrangement Reactions
4 Cyclization Reactions
5 Miscellaneous Reactions
6 Conclusion
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References
- 1a Meyer KH, Schuster K. Ber. Dtsch. Chem. Ges. 1922; 55: 819
- 1b Swaminathan S, Narayanan KV. Chem. Rev. 1971; 71: 429
- 1c Engel DA, Dudley GB. Org. Biomol. Chem. 2009; 7: 4149
- 1d Cadierno V, Crochet P, García-Garrido SE, Gimeno J. Dalton Trans. 2010; 39: 4015
-
2a Nicholas KM. Acc. Chem. Res. 1987; 20: 207
- 2b Tsuji J, Mandai T. Angew. Chem. Int. Ed. 1995; 34: 2589
- 2c Cadierno V, Gimeno J. Chem. Rev. 2009; 109: 3512
- 2d Nishibayashi Y. Synthesis 2012; 44: 489
- 2e Cadierno V, Crochet P, Gimeno J. Synlett 2008; 1105
- 2f Debleds O, Gayon E, Vrancken E, Campagne J.-M. Beilstein J. Org. Chem. 2011; 7: 866
- 2g Kalek M, Himo F. J. Am. Chem. Soc. 2012; 134: 19159
- 2h Hao L, Wu F, Ding Z.-C, Xu S.-X, Ma Y.-L, Chen L, Zhan Z.-P. Chem. Eur. J. 2012; 18: 6453
- 2i Heller ST, Kiho T, Narayan AR. H, Sarpong R. Angew. Chem. Int. Ed. 2013; 52: 11129
- 2j Ye J, Fan W, Ma S. Chem. Eur. J. 2013; 19: 716
- 2k Liu Z.-H, Liao PQ, Bi X.-H. Chem. Eur. J. 2014; 20: 17277
- 2l Fang Z.-X, Liu J.-Q, Liu Q, Bi X.-H. Angew. Chem. Int. Ed. 2014; 53: 7209
- 2m Liu Y, Barry B.-D, Yu H.-F, Liu J.-Q, Liao P.-Q, Bi X.-H. Org. Lett. 2013; 15: 2608
- 2n Sun L, Zhu Y.-X, Wang J, Lu P, Wang Y.-G. Org. Lett. 2015; 17: 242
- 3a Lipshutz BH, Yamamoto Y. Chem. Rev. 2008; 108: 2793
- 3b Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
- 3c Dias HV. R, Lovely CJ. Chem. Rev. 2008; 108: 3223
- 3d Majumdar KC, Sinha B. RSC Adv. 2014; 4: 8085
- 3e Barreiro EM, Adrio LA, Hii KK. M, Brazier JB. Eur. J. Org. Chem. 2013; 1027
- 3f Zhang D.-Y, Hu X.-P. Tetrahedron Lett. 2015; 56: 283
- 4a Bauer EB. Synthesis 2012; 44: 1131
- 4b Zhu Y, Sun L, Lu P, Wang Y. ACS Catal. 2014; 4: 1911
- 4c Biannic B, Aponick A. Eur. J. Org. Chem. 2011; 6605
-
4d Marion N, Nolan SP. Angew. Chem. Int. Ed. 2007; 46: 2750
- 4e Marco-Contelles J, Soriano E. Chem. Eur. J. 2007; 13: 1350
-
4f Shu X.-Z, Shu D.-X, Schienebeck CM, Tang W.-P. Chem. Soc. Rev. 2012; 41: 7698
- 4g Shiroodi RK, Gevorgyan V. Chem. Soc. Rev. 2013; 42: 4991
- 4h Tejedor D, Méndez-Abt G, Cotos L, García-Tellado F. Chem. Soc. Rev. 2013; 42: 458
- 5a Georgy M, Boucard V, Campagne J.-M. J. Am. Chem. Soc. 2005; 127: 14180
- 5b Georgy M, Boucard V, Debleds O, Zotto CD, Campagne J.-M. Tetrahedron 2009; 65: 1758
- 6 Liu J, Muth E, Florke U, Henkel G, Merz K, Sauvageau J, Schwake E, Dyker G. Adv. Synth. Catal. 2006; 348: 456
-
7 Reeds JP, Whitwood AC, Healy MP, Fairlamb IJ. S. Chem. Commun. 2010; 46: 2046
- 8 Pennell MN, Turner PG, Sheppard TD. Chem. Eur. J. 2012; 18: 4748
- 9 Hui H, Zhao Q, Yang M, She D, Chen M, Huang G. Synthesis 2008; 191
- 10 Yadav JS, Reddy BV, Rao TS, Rao KV. R. Tetrahedron Lett. 2008; 49: 614
- 11 Wang T, Chen X.-L, Chen L, Zhan Z.-P. Org. Lett. 2011; 13: 3324
- 12 Huang G.-B, Wang X, Pan Y.-M, Wang H.-S, Yao G.-Y, Zhang Y. J. Org. Chem. 2013; 78: 2742
- 13 Peng S.-Y, Wang L, Wang J. Org. Biomol. Chem. 2012; 10: 225
- 14 Zhang L, Zhu Y, Yin G, Lu P, Wang Y. J. Org. Chem. 2012; 77: 9510
- 15 Hao L, Pan Y, Wang T, Lin M, Chen L, Zhan Z. Adv. Synth. Catal. 2010; 352: 3215
- 16 Pan Y, Zhao S, Ji W, Zhan Z. J. Comb. Chem. 2009; 11: 103
- 17 Gujarathi S, Liu X, Song L, Hendrickson H, Zheng G. Tetrahedron 2014; 70: 5267
- 18 Debleds O, Zotto CD, Vrancken E, Campagne J.-M, Retailleau P. Adv. Synth. Catal. 2009; 351: 1991
- 19 Yoshimatsu M, Ohta K, Takahashi N. Chem. Eur. J. 2012; 18: 15602
- 20 Xu S.-X, Hao L, Wang T, Ding Z.-C, Zhan Z.-P. Org. Biomol. Chem. 2013; 11: 294
- 21 Lin M, Chen Q, Zhu Y, Chen X, Cai J, Pan Y, Zhan Z. Synlett 2011; 1179
- 22 Lee SI, Baek JY, Sim SH, Chung YK. Synthesis 2007; 2107
- 23 Lopez SS, Engel DA, Dudley GB. Synlett 2007; 949
- 24 Engel DA, Dudley GB. Org. Lett. 2006; 8: 4027
- 25 Engel DA, Lopez SS, Dudley GB. Tetrahedron 2008; 64: 6988
- 26 Ramóny RS, Marionz N, Nolan SP. Tetrahedron 2009; 65: 1767
- 27 Egi M, Yamaguchi Y, Fujiwara N, Akai S. Org. Lett. 2008; 10: 1867
- 28 Ye L, Zhang L. Org. Lett. 2009; 11: 3646
- 29 Pennell MN, Unthank MG, Turner P, Sheppard TD. J. Org. Chem. 2011; 76: 1479
- 30 Hansmann MM, Hashmi AS. K, Lautens M. Org. Lett. 2013; 15: 3226
- 31 Egi M, Umemura M, Kawai T, Akai S. Angew. Chem. Int. Ed. 2011; 50: 12197
- 32 Xu C.-F, Xu M, Yang L.-Q, Li C.-Y. J. Org. Chem. 2012; 77: 3010
- 33 Collins BS. L, Suero MG, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 5799
- 34a Xu Z.-F, Cai C.-X, Liu J.-T. Org. Lett. 2013; 15: 2096
- 34b Zhang G, Peng Y, Cui L, Zhang L. Angew. Chem. Int. Ed. 2009; 48: 3112
- 35 Xiong Y, Wu M.-Y, Zhang X.-Y, Ma C.-L, Huang L, Zhao L.-J, Tan B, Liu X.-Y. Org. Lett. 2014; 16: 1000
- 36 Kang Y.-W, Choi Y.-J, Jang H.-Y. Org. Lett. 2014; 16: 4842
- 37 Li G, Zhang L.-M. Angew. Chem. Int. Ed. 2007; 46: 5156
- 38 Zhang L.-M. Acc. Chem. Res. 2014; 47: 877
- 39 Yeom H.-S, Lee Y, Jeong J, So E, Hwang S, Lee J.-E, Lee S.S, Shin S. Angew. Chem. Int. Ed. 2010; 49: 1611
- 40 Ye L, He W, Zhang L. J. Am. Chem. Soc. 2010; 132: 8550
- 41 Hashmi AS. K, Wang T, Shi S, Rudolph M. J. Org. Chem. 2012; 77: 7761
- 42 Noey EL, Luo Y.-D, Zhang L.-M, Houk KN. J. Am. Chem. Soc. 2012; 134: 1078
- 43 Wang T, Shi S, Hansmann MM, Rettenmeier E, Rudolph M, Hashmi AS. K. Angew. Chem. Int. Ed. 2014; 53: 3715
- 44 Wang L, Xie X, Liu Y. Angew. Chem. Int. Ed. 2013; 52: 13302
- 45 Biswas S, Samec JS. M. Chem. Commun. 2012; 48: 6586
- 46 Biswas S, Dahlstrand C, Watile RA, Kalek M, Himo F, Samec JS. M. Chem. Eur. J. 2013; 19: 17939
- 47 Biswas S, Watile RA, Samec JS. M. Chem. Eur. J. 2014; 20: 2159
- 48 Cadu A, Watile RA, Biswas S, Orthaber A, Sjöberg PJ. R, Samec JS. M. Org. Lett. 2014; 16: 5556
- 49 Watile RA, Biswas S, Samec JS. M. Green Chem. 2013; 15: 3176
- 50 D’Oyley JM, Aliev AE, Sheppard TD. Angew. Chem. Int. Ed. 2014; 53: 10747
- 51a Crabbé P, Fillion H, André D, Luche J.-L. J. Chem. Soc., Chem. Commun. 1979; 859
- 51b Searles S, Li Y, Nassim B, Lopes M.-TR, Tran PT, Crabbé P. J. Chem. Soc., Perkin Trans. 1 1984; 747
- 52 Ma S, Hou H, Zhao S, Wang G. Synthesis 2002; 1643
- 53 Kuang J, Xie X, Ma S. Synthesis 2013; 45: 592
- 54 Suarez A, Fu GC. Angew. Chem. Int. Ed. 2004; 43: 3580
- 55 Sabbasani VR, Mamidipalli P, Lu H, Xia Y, Lee D. Org. Lett. 2013; 15: 1552
- 56 Liu J, Liu Z, Wu N, Liao P, Bi X. Chem. Eur. J. 2014; 20: 2154
- 57 Ye J, Li S, Chen B, Fan W, Kuang J, Liu J, Liu Y, Miao B, Wan B, Wang Y, Xie X, Yu Q, Yuan W, Ma S. Org. Lett. 2012; 14: 1346
- 58 Fan W, Ma S.-M. Chem. Commun. 2013; 49: 10175
- 59 Fan W, Yuan W, Ma S.-M. Nat. Commun. 2014; 5: 3884
- 60 Fan W, Ma S. Angew. Chem. Int. Ed. 2014; 53: 14542
- 61 Kim SM, Lee D, Hong SH. Org. Lett. 2014; 16: 6168
- 62a Hayes SJ, Knight DW, Menzies MD, O’Halloran M, Tan W. Tetrahedron Lett. 2007; 48: 7709
- 62b Sharland CM, Singkhonrat J, NajeebUllah M, Hayes SJ, Knight DW, Dunford DG. Tetrahedron Lett. 2011; 52: 2320
- 62c Aponick A, Li C.-Y, Malinge J, Marques EF. Org. Lett. 2009; 11: 4624
- 62d Egi M, Azechi K, Akai S. Org. Lett. 2009; 11: 5002
- 62e Egi M, Azechi K, Akai S. Adv. Synth. Catal. 2011; 353: 287
- 62f Minkler SR. K, Isley NA, Lippincott DJ, Krause N, Lipshutz BH. Org. Lett. 2014; 16: 724
- 63 Kothandaraman P, Rao W.-D, Foo SJ, Chan PW. H. Angew. Chem. Int. Ed. 2010; 49: 4619
- 64 Kothandaraman P, Mothe SR, Toh SS. M, Chan PW. H. J. Org. Chem. 2011; 76: 7633
- 65 Dhiman S, Ramasastry SS. V. Chem. Commun. 2015; 51: 557
- 66 Mothe SR, Kothandaraman P, Lauw SJ. L, Chin SM. W, Chan PW. H. Chem. Eur. J. 2012; 18: 6133
- 67 Susanti D, Koh F, Kusuma JA, Kothandaraman P, Chan PW. H. J. Org. Chem. 2012; 77: 7166
- 68 Mothe SR, Novianti ML, Ayers BJ, Chan PW. H. Org. Lett. 2014; 16: 4110
- 69 Zhang J, Shao J.-D, Xue J.-J, Wang Y.-X, Li Y. RSC Adv. 2014; 4: 63850
- 70 Liu J.-Q, Liu Z.-H, Liao P.-Q, Bi X.-H. Org. Lett. 2014; 16: 6204
- 71 Li H, Li X, Wang H.-Y, Winston-McPherson GN, Geng H.-mJ, Guzei IA, Tang W. Chem. Commun. 2014; 50: 12293
- 72 Cera G, Piscitelli S, Chiarucci M, Fabrizi G, Goggiamani A, Ramόn RS, Nolan SP, Bandini M. Angew. Chem. Int. Ed. 2012; 51: 9891
- 73 Chiarucci M, Matteucci E, Cera G, Fabrizi G, Bandini M. Chem. Asian J. 2013; 8: 1776
- 74 Wang T, Shi S, Pflästerer D, Rettenmeier E, Rudolph M, Rominger F, Hashmi AS. K. Chem. Eur. J. 2014; 20: 292
- 75 Shu X.-Z, Liu X.-Y, Xiao H.-Q, Ji K.-G, Guo L.-N, Liang Y.-M. Adv. Synth. Catal. 2008; 350: 243
- 76 Yan B, Zhou Y, Zhang H, Chen J, Liu Y. J. Org. Chem. 2007; 72: 7783
- 77 Meng X, Liao P, Liu J, Bi X. Chem. Commun. 2014; 50: 11837
- 78 Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123
- 79 Ramón RS, Pottier C, Gómez-Suárez A, Nolan SP. Adv. Synth. Catal. 2011; 353: 1575
- 80 Pennell MN, Foster RW, Turner PG, Hailes HC, Tame CJ, Sheppard TD. Chem. Commun. 2014; 50: 1302
- 81 Aponick A, Li C.-Y, Palmes JA. Org. Lett. 2009; 11: 121
- 82 Egi M, Ota Y, Nishimura Y, Shimizu K, Azechi K, Akai S. Org. Lett. 2013; 15: 4150
- 83 Dai LZ, Shi M. Chem. Eur. J. 2008; 14: 7011
- 84a Kikuchi S, Yamada T. Chem. Rec. 2014; 14: 62
- 84b Kikuchi S, Yoshida S, Sugawara Y, Yamada W, Cheng H.-M, Fukui K, Sekine K, Iwakura I, Ikeno T, Yamada T. Bull. Chem. Soc. Jpn. 2011; 84: 698
- 85 Yamada W, Sugawara Y, Cheng HM, Ikeno T, Yamada T. Eur. J. Org. Chem. 2007; 2604
- 86 Ugajin R, Kikuchi S, Yamada T. Synlett 2014; 25: 1178
- 87 Song Q.-W, Yu B, Li X.-D, Ma R, Diao Z.-F, Li R.-G, Li W, He L.-N. Green Chem. 2014; 16: 1633
- 88a Laas H, Nissen A, Nürrenbach A. Synthesis 1981; 958
- 88b Jiang H.-F, Wang A-Z, Liu H.-L, Qi C.-R. Eur. J. Org. Chem. 2008; 2309
- 88c Gu Y.-L, Shi F, Deng Y.-Q. J. Org. Chem. 2004; 69: 391
- 89 Tang X.-D, Qi C.-R, He HT, Jiang H.-F, Ren Y.-W, Yuan G.-Q. Adv. Synth. Catal. 2013; 355: 2019
- 90 Sugawara Y, Yamada W, Yoshida S, Ikeno T, Yamada T. J. Am. Chem. Soc. 2007; 129: 12902
- 91 He H, Qi C, Hu X, Guan Y, Jiang H. Green Chem. 2014; 16: 3729
- 92 Qi C, Jiang H, Huang L, Yuan G, Ren Y. Org. Lett. 2011; 13: 5520
- 93 Fehr C, Farris I, Sommer H. Org. Lett. 2006; 8: 1839
- 94 Grisé CM, Barriault L. Org. Lett. 2006; 8: 5905
- 95 Grisé CM, Rodrigue EM, Barriault L. Tetrahedron 2008; 64: 797
- 96 Chen Y, Wang L, Sun N, Xie X, Zhou X, Chen H, Li Y, Liu Y. Chem. Eur. J. 2014; 20: 12015
- 97 Cao H, Jiang H.-F, Yao W.-J, Liu X.-H. Org. Lett. 2009; 11: 1931
- 98 Cao H, Jiang H.-F, Mai R.-H, Zhu S.-F, Qi C.-R. Adv. Synth. Catal. 2010; 352: 143
-
99 Yao L.-F, Wei Y, Shi M. J. Org. Chem. 2009; 74: 9466
- 100 Lian J.-J, Liu RS. Chem. Commun. 2007; 1337
-
101 Lauterbach T, Arndt S, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2013; 355: 1755
- 102 Chen Y.-F, Li G.-J, Liu Y.-H. Adv. Synth. Catal. 2011; 353: 392
- 103 Chen Y.-F, Chen M, Liu Y.-H. Angew. Chem. Int. Ed. 2012; 51: 6181
- 104 Chen Z.-Y, Zeng M.-J, Yuan J.-J, Yang Q, Peng Y.-Y. Org. Lett. 2012; 14: 3588
- 105 Chen Z.-Y, Jia X.-G, Ye C.-Q, Qiu G, Wu J. Chem. Asian J. 2014; 9: 126
- 106 Teo WT, Rao W, Ng CJ. H, Koh SW. Y, Chan PW. H. Org. Lett. 2014; 16: 1248
-
107 Markham JP, Staben ST, Toste FD. J. Am. Chem. Soc. 2005; 127: 9708
- 108 Kim K.-D, Yeom H.-S, Shin S, Shin S. Tetrahedron 2012; 68: 5241
- 109 An J.-H, Yun H, Shin S, Shin S. Adv. Synth. Catal. 2014; 356: 3749
- 110 Zhu D.-Y, Zhang Z, Mou X.-Q, Tu Y.-Q, Zhang F.-M, Peng J.-B, Wang S.-H, Zhang S.-Y. Adv. Synth. Catal. 2015; 357: 747
- 111 Zhang Q.-W, Xiang K, Tu Y.-Q, Zhang S.-Y, Zhang X.-M, Zhao Y.-M, Zhang T.-C. Chem. Asian J. 2012; 7: 894
- 112 Han C, Yu M, Sun W, Yao X. Synlett 2011; 2363
- 113 Lv W, Tian J, Deng N, Wang Y, Zhu X.-S, Yao X.-Q. Tetrahedron Lett. 2015; 56: 1312
- 114 Weerasiri KC, Gorden AE. V. Eur. J. Org. Chem. 2013; 1546
- 115 Peng H, Xi Y, Ronaghi N, Dong B, Akhmedov NG, Shi X. J. Am. Chem. Soc. 2014; 136: 13174
- 116a Bae I, Han H, Chang S. J. Am. Chem. Soc. 2005; 127: 2038
- 116b Yoo EJ, Bae I, Cho SH, Han H, Chang S. Org. Lett. 2006; 8: 1347
- 117 Cho SH, Chang S. Angew. Chem. Int. Ed. 2007; 46: 1897
- 118 Liu Z, Liu J, Zhang L, Liao P, Song J, Bi X. Angew. Chem. Int. Ed. 2014; 53: 5305
For selected recent examples, see:
Some reviews on coinage-metal-catalyzed reactions: