Gold Catalysis and Furans: A Powerful Match for Synthetic Connections

Abstract

This review summarizes the advances made on the synthesis and functionalization of furans via gold catalysis during the period between 2016 and 2020. A separate section is dedicated to the tandem gold-catalyzed synthesis and functionalization of furans.

1 Introduction

2 Gold-Catalyzed Synthesis of Furans

2.1 Cycloisomerizations of Alkynyl and Cumulenyl Alcohols

2.2 Cycloisomerizations of Alkynyl and Allenyl Ketones

2.3 Reactions with External Oxidants

2.4 Miscellaneous

3 Gold-Catalyzed Functionalization of Furans

3.1 Cycloadditions

3.2 Furan Ring Decorations

3.3 Reactions Involving Furan Ring Opening

4 Gold-Catalyzed Tandem Synthesis and Functionalization of Furans­

4.1 Cycloisomerizations Followed by Gold-Catalyzed Cycloaddition

4.2 Cycloisomerizations to a Gold 1,3- or 1,4-Dipole and Intermolecular Annulation

4.3 Cycloisomerizations to a Gold Carbene and Intermolecular Trapping

5 Conclusion

Key words

gold - furans - tandem reactions - alkynes - cycloisomerization - ring opening - cycloaddition

Publikationsverlauf

Eingereicht: 05. Oktober 2020

Angenommen nach Revision: 05. November 2020

Artikel online veröffentlicht:
21. Dezember 2020

• References


For the first report, see:
• 1a Hashmi AS. K, Frost TM, Bats J. J. Am. Chem. Soc. 2000; 122: 11553

For selected mechanistic studies, see:
• 1b Hashmi AS. K, Rudolph M, Weyrauch JP, Wölfle M, Frey W, Bats JW. Angew. Chem. Int. Ed. 2005; 44: 2798
• 1c Echavarren AM, Méndez M, Muñoz MP, Nevado C, Martín-Matute B, Nieto-Oberhuber C, Cárdenas DJ. Pure Appl. Chem. 2004; 76: 453

For selected examples of synthesis, see:
• 1d Hashmi AS. K, Rudolph M, Siehl HU, Tanaka M, Bats JW, Frey W. Chem. Eur. J. 2008; 14: 3703
• 1e Hashmi AS. K, Weyrauch JP, Kurpejović E, Frost TM, Miehlich B, Frey W, Bats JW. Chem. Eur. J. 2006; 12: 5806
• 1f Hashmi AS. K, Rudolph M, Huck J, Frey W, Bats JW, Hamzić M. Angew. Chem. Int. Ed. 2009; 48: 5848
• 1g Hashmi AS. K, Salathé R, Frey W. Chem. Eur. J. 2006; 12: 6991
• 1h Zeiler A, Ziegler MJ, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2015; 357: 1507
• 2a Ahlsten N, Cambeiro XC, Perry GJ, Larrosa I. C–H Functionalisation of Heteroaromatic Compounds via Gold Catalysis. In Au-Catalyzed Synthesis and Functionalization of Heterocycles: Topics in Heterocyclic Chemistry, Vol. 46. Bandini M. Springer International Publishing; Switzerland: 2016: 175-226
• 2b Kirillova MS, Miloserdov FM, Echavarren AM. Hydro­arylation of Alkynes using Cu, Ag, and Au Catalysts . In Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, Chap. 7. Ackermann L, Gunnoe TB, Habgood LG. Wiley-VCH; Weinheim: 2018
• 2c de Mendoza P, Echavarren AM. Intramolecular Hydroarylation of Alkynes . In Modern Gold Catalyzed Synthesis . Hashmi SK, Toste DF. Wiley-VCH; Weinheim: 2012: 135-152
• 2d Muratore ME, Echavarren AM. Gold-Catalyzed Hydroarylation of Alkynes. In PATAI’S Chemistry of Functional Groups. John Wiley & Sons; Chichester: 2009: 1-96
• 3a Blanc A, Beneteau V, Weibel J.-M, Pale P. Org. Biomol. Chem. 2016; 14: 9184
• 3b Arcadi A. Gold-Catalyzed Synthesis of Heterocycles . In Gold Catalysis: An Homogeneous Approach . Toste FD, Michelet V. Imperial College Press; London: 2014: 175-224
• 4 Hashmi AS. K, Häffner T, Rudolph M, Rominger F. Chem. Eur. J. 2011; 17: 8195
• 5 The use of Au catalysts for the oxidative conversions of furfural and 5-hydroxymethylfurfural is not covered, since in this case the reactivity of the aldehyde moiety, and not of the furan ring itself, is involved.
• 6 Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
• 7a Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
• 7b Krause N, Winter C. Chem. Rev. 2011; 111: 1994
• 8 Klenk S, Rupf S, Suntrup L, van der Meer M, Sarkar B. Organometallics 2017; 36: 2026
• 9 Lempke L, Ernst A, Kahl F, Weberskirch R, Krause N. Adv. Synth. Catal. 2016; 358: 1491
• 10 Riedel S, Maier ME. J. Org. Chem. 2020; 85: 8203
• 11 Riedel S, Maichle-Mössmer C, Maier ME. J. Org. Chem. 2017; 82: 12798
• 12 Praveen C, Perumal PT. Chin. J. Catal. 2016; 37: 288
• 13 Chen HF, Yeh MC. P. J. Chin. Chem. Soc. 2019; 66: 614
• 14 Liu W.-T, Xu Z.-L, Mou X.-Q, Zhang B.-H, Bao W, Wang S.-H, Lee D, Lei L.-S, Zhang K. Org. Biomol. Chem. 2017; 15: 6333
• 15 Hamel J.-D, Paquin J.-F. J. Fluorine Chem. 2018; 216: 11
• 16 Alcaide B, Almendros P, Cembellin S, Fernandez I, Martinez del Campo T. Chem. Eur. J. 2016; 22: 11667
• 17a Alcaide B, Almendros P, Alonso JM, Quiros MT, Gadzinski P. Adv. Synth. Catal. 2011; 353: 1871
• 17b Kong W, Fu C, Ma S. Chem. Eur. J. 2011; 17: 13134
• 18 Gubaidullin RR, Khalitova RR, Galimshina ZR, Spivak AY. Tetrahedron 2018; 74: 1888
• 19 Ge S, Zhang Y, Tan Z, Li D, Dong S, Liu X, Feng X. Org. Lett. 2020; 22: 3551
• 20 Zhang C, Jiang H, Zhu S. Chem. Commun. 2017; 53: 2677
• 21 Hu X, Zhou B, Jin H, Liu Y, Zhang L. Chem. Commun. 2020; 56: 7297
• 22a Li X, Ma X, Wang Z, Liu PN, Zhang L. Angew. Chem. Int. Ed. 2019; 58: 17180
• 22b Wang H, Li T, Zheng Z, Zhang L. ACS Catal. 2019; 9: 10339
• 23 Zorba L, Kidonakis M, Saridakis I, Stratakis M. Org. Lett. 2019; 21: 5552
• 24 Xue C, Huang X, Wu S, Fu C, Ma S. Org. Chem. Front. 2016; 3: 588
• 25 Cheng X, Yu Y, Mao Z, Chen J, Huang X. Org. Biomol. Chem. 2016; 14: 3878
• 26 Miura T, Tanaka T, Matsumoto K, Murakami M. Chem. Eur. J. 2014; 20: 16078
• 27a Zhang L. Acc. Chem. Res. 2014; 47: 877
• 27b Yeom H.-S, Shin S. Acc. Chem. Res. 2014; 47: 966
• 27c Bhunia S, Ghosh P, Patra SR. Adv. Synth. Catal. 2020; 362: 3664
• 28 Rode N, Marinelli F, Arcadi A, Adak T, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2018; 360: 4790
• 29 Li J, Xing H.-W, Yang F, Chen Z.-S, Ji K. Org. Lett. 2018; 20: 4622
• 30 Hamada N, Yamaguchi A, Inuki S, Oishi S, Ohno H. Org. Lett. 2018; 20: 4401
• 31 Zhang B, Wang T, Zhang Z. J. Org. Chem. 2017; 82: 11644
• 32 Zang W, Wei Y, Shi M. Chem. Commun. 2019; 55: 8126
• 33 Nagaraju V, Raju CE, Purnachandar D, Rao VJ, Karunakar GV. ChemistrySelect 2019; 4: 2053

For other examples of 1,2-iodine shifts in gold catalysis, see:
• 34a Morán-Poladura P, Rubio E, González JM. Beilstein J. Org. Chem. 2013; 9: 2120
• 34b Noesel P, Mueller V, Mader S, Moghimi S, Rudolph M, Braun I, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2015; 357: 500
• 34c Morán-Poladura P, Rubio E, Gonzalez JM. Angew. Chem. Int. Ed. 2015; 54: 3052
• 35 Fernández-Canelas P, Rubio E, González JM. Org. Lett. 2019; 21: 6566
• 36 Bao M, Qian Y, Su H, Wu B, Qiu L, Hu W, Xu X. Org. Lett. 2018; 20: 5332
• 37 Liao J, Guo P, Chen Q. Catal. Commun. 2016; 77: 22
• 38a Wei C, Li C.-J. J. Am. Chem. Soc. 2003; 125: 9584
• 38b Wei C, Li Z, Li C.-J. Synlett 2004; 1472
• 39 Li J, Rudolph M, Rominger F, Xie J, Hashmi AS. K. Adv. Synth. Catal. 2016; 358: 207
• 40 Ma R, Yang J, Kelley S, Gung BW. J. Organomet. Chem. 2019; 898: 120865
• 41a Gung BW, Conyers RC, Wonser J. Synlett 2013; 24: 1238
• 41b Yang JM, Tang XY, Shi M. Chem. Eur. J. 2015; 21: 4534
• 42 Ma R, Gung BW. Tetrahedron 2020; 76: 130840
• 43a Wang S, Zhang G, Zhang L. Synlett 2010; 692
• 43b Shiroodi RK, Gevorgyan V. Chem. Soc. Rev. 2013; 42: 4991
• 43c Correa A, Marion N, Fensterbank L, Malacria M, Nolan SP, Cavallo L. Angew. Chem. Int. Ed. 2008; 47: 718
• 44 Sun N, Xie X, Chen H, Liu Y. Chem. Eur. J. 2016; 22: 14175
• 45 Drew MA, Arndt S, Richardson C, Rudolph M, Hashmi AS. K, Hyland CJ. Chem. Commun. 2019; 55: 13971
• 46 Widstrom AL, Lear BJ. Appl. Nanosci. 2020; 10: 819
• 47 Xu G, Liu K, Sun J. Org. Lett. 2018; 20: 72
• 48 Zhai RL, Xue YS, Liang T, Mi JJ, Xu Z. J. Org. Chem. 2018; 83: 10051
• 49 Sanz-Vidal A, Miro J, Sanchez-Rosello M, Del Pozo C, Fustero S. J. Org. Chem. 2016; 81: 6515
• 50 Pirovano V, Brambilla E, Rizzato S, Abbiati G, Bozzi M, Rossi E. J. Org. Chem. 2019; 84: 5150
• 51 Ibáñez S, Poyatos M, Dawe LN, Gusev D, Peris E. Organometallics 2016; 35: 2747
• 52 Du X, Yu J, Gong J, Zaman M, Pereshivko OP, Peshkov VA. Eur. J. Org. Chem. 2019; 2502
• 53 Brambilla E, Pirovano V, Giannangeli M, Abbiati G, Caselli A, Rossi E. Org. Chem. Front. 2019; 6: 3078
• 54 Zhao Y.-L, Cao Z.-Y, Zeng X.-P, Shi J.-M, Yu Y.-H, Zhou J. Chem. Commun. 2016; 52: 3943
• 55 Miedziak PJ, Edwards JK, Taylor SH, Knight DW, Tarbit B, Hutchings GJ. Catal. Lett. 2018; 148: 2109
• 56 Li Y, Wei M, Dai M. Tetrahedron 2017; 73: 4172
• 57 Li Y, Dai M. Angew. Chem. Int. Ed. 2017; 56: 11624
• 58 For a review on gold 1,n-dipoles, see: Garayalde D, Nevado C. ACS Catal. 2012; 2: 1462
• 59 Liu S, Yang P, Peng S, Zhu C, Cao S, Li J, Sun J. Chem. Commun. 2017; 53: 1152
• 60 Du Q, Neudörfl JM, Schmalz HG. Chem. Eur. J. 2018; 24: 2379
• 61 Di X, Wang Y, Wu L, Zhang Z.-M, Dai Q, Li W, Zhang J. Org. Lett. 2019; 21: 3018
• 62 Zhou L, Xu B, Ji D, Zhang ZM, Zhang J. Chin. J. Chem. 2020; 38: 577
• 63 Yan D, Wang N, Xue T, Wu H, Zhang J, Wu P. ChemCatChem 2020; 12: 4067
• 64 Wang Y, Zhang Z.-M, Liu F, He Y, Zhang J. Org. Lett. 2018; 20: 6403
• 65 Gao H, Wu X, Zhang J. Chem. Eur. J. 2011; 17: 2838
• 66 Qi J, Teng Q, Thirupathi N, Tung C.-H, Xu Z. Org. Lett. 2019; 21: 692
• 67 Zhang S, Tang A, Chen P, Zhao Z, Miao M, Ren H. Org. Lett. 2020; 22: 848
• 68 Miao M, Xu H, Jin M, Chen Z, Xu J, Ren H. Org. Lett. 2018; 20: 3096
• 69 Liu P, Sun J. Org. Lett. 2017; 19: 3482
• 70 Purnachandar D, Suneel K, Balasubramanian S, Karunakar GV. Org. Biomol. Chem. 2019; 17: 4856