Progress in the field of catalytic alkylation of furans by π-activated alcohols over the last 15 years is reviewed. The occurence of benzyl-, allyl-, and propargylfurans in natural sources and their biological activity is also discussed.
Similar content being viewed by others
References
P. Gallezot, Chem. Soc. Rev., 41, 1538 (2012).
F. W. Lichtenthaler and S. Peters, C. R. Chimie, 7, 65 (2004).
M. Besson, P. Gallezot, and C. Pinel, Chem. Rev., 114, 1827 (2014).
A. A. Rosatella, S. P. Simeonov, R. F. M. Frade, and C. A. M. Afonso, Green Chem., 13, 754 (2011).
S. P. Roche and J. A. Porco, Jr., Angew. Chem., Int. Ed., 50, 4068 (2011).
T. J. Donohoe and R. D. C. Pullin, Chem. Commun., 48, 11924 (2012).
L. Hu, G. Zhao, W. Hao, X. Tang, Y. Sun, L. Lin, and S. Liu, RSC Adv., 2, 11184 (2012).
C. D. Vanderwal, J. Org. Chem., 76, 9555 (2011).
N. Mori and Y. Kuwahara, J. Chem. Ecol., 26, 1299 (2000).
B. Y. Hwang, J.-H. Lee, J. B. Nam, H. S. Kim, Y. S. Hong, and J. J. Lee, J. Nat. Prod., 65, 616 (2002).
S.-Y. Cheng, K.-J. Huang, S.-K. Wang, Z.-H. Wen, P.-W. Chen, and C.-Y. Duh, J. Nat. Prod., 73, 771 (2010).
H. Meng, G. Li, J. Huang, K. Zhang, X. Wei, Y. Ma, C. Zhang, and J. Wang, Phytochemistry, 86, 151 (2013).
K. Kojima, K. Isaka, O. Purev, G. Jargalsaikhan, D. Suran, H. Mizukami, and Y. Ogihara, Chem. Pharm. Bull., 47, 690 (1999).
T. Motai and S. Kitanaka, Chem. Pharm. Bull., 52, 1215 (2004).
K. M. Fisch, V. Böhm, A. D. Wright, and G. M. König, J. Nat. Prod., 66, 968 (2003).
Q. Göthel, J. Muñoz, and M. Köck, Phytochemistry Lett., 5, 693 (2012).
R. J. Clark, M. J. Garson, I. M. Brereton, and J. A. Kennedy, J. Nat. Prod., 62, 915 (1999).
K.-J. Wang, C.-C. Zhu, L. Di, N. Li, and Y.-X. Zhao, Fitoterapia, 81, 869 (2010).
N. An, H.-W. Zhang, L.-Z. Xu, S.-L. Yang, and Z.-M. Zou, Food Chem., 119, 513 (2010).
Y. Sun, K. Tabata, H. Matsubara, S. Kitanaka, T. Suzuki, and K. Yasukawa, Planta Med., 74, 427 (2008).
K. L. McPhail, D. E. A. Rivett, D. E. Lack, and M. T. Davies-Coleman, Tetrahedron, 56, 9391 (2000).
D. M. Soderlund, Arch. Toxicol., 86, 165 (2012).
M. J. Wolansky and J. A. Harrill, Neurotoxicol. Teratol., 30, 55 (2008).
E. D. Clercq, J. Med. Chem., 48, 1297 (2005).
Y. Pommier, A. A. Johnson, and C. Marchand, Nature Rev. Drug Discov., 4, 236 (2005).
L. S. Glass, A. Bapat, M. R. Kelley, M. M. Georgiadis, and E. C. Long, Bioorg. Med. Chem. Lett., 20, 1685 (2010).
S. K. Chauthe, S. B. Bharate, S. Sabde, D. Mitra, K. K. Bhutani, and I. P. Singh, Bioorg. Med. Chem., 18, 2029 (2010).
N. Yamakawa, S. Suemasu, Y. Okamoto, K.-I. Tanaka, T. Ishihara, T. Asano, K. Miyata, M. Otsuka, and T. Mizushima, J. Med. Chem., 55, 5143 (2012).
T. D. Penning, N. S. Chandrakumar, B. B. Chen, H. Y. Chen, B. N. Desai, S. W. Djuric, S. H. Docter, A. F. Gasiecki, R. A. Haack, J. M. Miyashiro, M. A. Russell, S. S. Yu, D. G. Corley, R. C. Durley, B. F. Kilpatrick, B. L. Parnas, L. J. Askonas, J. K. Gierse, E. I. Harding, M. K. Highkin, J. F. Kachur, S. H. Kim, G. G. Krivi, D. Villani-Price, E. Y. Pyla, W. G. Smith, and N. S. Ghoreishi-Haack, J. Med. Chem., 43, 721 (2000).
C.-H. Lee and W.-S. Cho, Tetrahedron Lett., 40, 8879 (1999).
F. Mühlthau, O. Schuster, and T. Bach, J. Am. Chem. Soc., 127, 9348 (2005).
P. Rubenbauer and T. Bach, Adv. Synth. Catal., 350, 1125 (2008).
A. V. Butin, T. A. Stroganova, I. V. Lodina, and G. D. Krapivin, Tetrahedron Lett., 42, 2031 (2001).
A. V. Butin, S. K. Smirnov, T. A. Stroganova, W. Bender, and G. D. Krapivin, Tetrahedron, 63, 474 (2007).
L. Chen and J. Zhou, Chem. – Asian J., 7, 2510 (2012).
D. Yu. Kosulina, V. K. Vasilin, T. A. Stroganova, E. A. Sbitneva, A. V. Butin, and G. D. Krapivin, Khim. Geterotsikl. Soedin., 1380 (2009). [Chem. Heterocycl. Compd., 45, 1105 (2009).]
D. Yu. Kosulina, V. K. Vasilin, T. A. Stroganova, T. Ya. Kaklyugina, and G. D. Krapivin, J. Heterocycl. Chem., 47, 309 (2010).
S. Shirakawa and S. Kobayashi, Org. Lett., 9, 311 (2007).
J. L. Bras and J. Muzart, Tetrahedron, 63, 7942 (2007).
O. Mendoza, G. Rossey, and L. Ghosez, Tetrahedron Lett., 52, 2235 (2011).
A. Kuznetsov, A. Makarov, A. E. Rubtsov, A. V. Butin, and V. Gevorgyan, J. Org. Chem., 78, 12144 (2013).
M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, and K. Ishii, J. Org. Chem., 68, 9340 (2003).
M. Noji, H. Sunahara, K.-I. Tsuchiya, T. Mukai, A. Komasaka, and K. Ishii, Synthesis, 3835 (2008).
K. Mertins, I. Iovel, J. Kischel, A. Zapf, and M. Beller, Angew. Chem., Int. Ed., 44, 238 (2005).
I. Iovel, K. Mertins, J. Kischel, A. Zapf, and M. Beller, Angew. Chem., Int. Ed., 44, 3913 (2005).
K. Mertins, I. Iovel, J. Kischel, A. Zapf, and M. Beller, Adv. Synth. Catal., 348, 691 (2006).
F.-Q. Yuan, L.-X. Gao, and F.-S. Han, Chem. Commun., 47, 5289 (2011).
J. Gao, J.-Q. Wang, Q.-W. Song, and L.-N. He, Green Chem., 13, 1182 (2011).
J. A. McCubbin and O. V. Krokhin, Tetrahedron Lett., 51, 2447 (2010).
Y. Sato, T. Aoyama, T. Takido, and M. Kodomari, Tetrahedron, 68, 7077 (2012).
S. Podder and S. Roy, Tetrahedron, 63, 9146 (2007).
S. Podder, J. Choudhury, U. K. Roy, and S. Roy, J. Org. Chem., 72, 3100 (2007).
S. Podder, J. Choudhury, and S. Roy, J. Org. Chem., 72, 3129 (2007).
A. K. Maity, P. N. Chatterjee, and S. Roy, Tetrahedron, 69, 942 (2013).
Z. Li, Z. Duan, H. Wang, R. Tian, Q. Zhu, and Y. Wu, Synlett, 2535 (2008).
Z. Li, Z. Duan, J. Kang, H. Wang, L. Yu, and Y. Wu, Tetrahedron, 64, 1924 (2008).
Z. Liu, D. Wang, and Y. Chen, Lett. Org. Chem., 8, 73 (2011).
Y.-L. Liu, L. Liu, Y.-L. Wang, Y.-C. Han, D. Wang, and Y.-J. Chen, Green Chem., 10, 635 (2008).
Z. Liu, D. Wang, Y. Wu, and Y. Chen, Synth. Commun., 42, 1813 (2012).
G. Onodera, H. Imajima, M. Yamanashi, Y. Nishibayashi, M. Hidai, and S. Uemura, Organometallics, 23, 5841 (2004).
G.-Q. Chen, Z.-J. Xu, S. L.-F. Chan, C.-Y. Zhou, and C.-M. Che, Synlett, 2713 (2011).
P. N. Chatterjee and S. Roy, Tetrahedron, 68, 3776 (2012).
A. V. Malkov, S. L. Davis, I. R. Baxendale, W. L. Mitchell, and P. Kočovský, J. Org. Chem., 64, 2751 (1999).
D. Das, S. Pratihar, U. K. Roy, D. Mal, and S. Roy, Org. Biomol. Chem., 10, 4537 (2012).
F.-Q. Yuan, F.-Y. Sun, and F.-S. Han, Tetrahedron, 68, 6837 (2012).
Y. Chen, Y. Lu, G. Li, and Y. Liu, Org. Lett., 11, 3838 (2009).
Y. Chen and Y. Liu, J. Org. Chem., 76, 5274 (2011).
Y.-C.Wu, H.-J. Li, L. Liu, N. Demoulin, Z. Liu, D. Wang, and Y.-J. Chen, Adv. Synth. Catal., 353, 907 (2011).
Z.-P. Zhan, Y.-Y. Cui, and H.-J. Liu, Tetrahedron Lett., 47, 9143 (2006).
Z.-P. Zhan, J.-L. Yu, H.-J. Liu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, and J.-P. Li, J. Org. Chem., 71, 8298 (2006).
M. Lin, L. Hao, X.-T. Liu, Q.-Z. Chen, F. Wu, P. Yan, S.-X. Xu, X.-L. Chen, J.-J Wen, and Z.-P Zhan, Synlett, 665 (2011).
J. S. Yadav, B. V. Subba Reddy, K. V. Raghavendra Rao, and G. G. K. S. Narayana Kumar, Synthesis, 3205 (2007).
J. S. Yadav, B. V. Subba Reddy, K. V. Raghavendra Rao, and G. G. K. S. Narayana Kumar, Tetrahedron Lett., 48, 5573 (2007).
G. Aridoss, V. D. Sarca, J. F. Ponder Jr., J. Crowe, and K. K. Laali, Org. Biomol. Chem., 9, 2518 (2011).
C. C. Silveira, S. R. Mendes, and G. M. Martins, Tetrahedron Lett., 53, 1567 (2012).
M. Georgy, V. Boucard, and J.-M. Campagne, J. Am. Chem. Soc., 127, 14180 (2005).
M. Georgy, V. Boucard, O. Debleds, C. D. Zotto, and J.-M. Campagne, Tetrahedron, 65, 1758 (2009).
Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, and S. Uemura, Angew. Chem., Int. Ed., 42, 1495 (2003).
P. N. Chatterjee and S. Roy, J. Org. Chem., 75, 4413 (2010).
E. Bustelo and P. H. Dixneuf, Adv. Synth. Catal., 347, 393 (2005).
C. Fischmeister, L. Toupet, and P. H. Dixneuf, New J. Chem., 29, 765 (2005).
E. Busteloa and P. H. Dixneuf, Adv. Synth. Catal., 349, 933 (2007).
J. J. Kennedy-Smith, L. A. Young, and F. D. Toste, Org. Lett., 6, 1325 (2004).
Y. Kuninobu, H. Ueda, and K. Takai, Chem. Lett., 37, 878 (2008).
R. Sanz, A. Martínez, J. M. Álvarez-Gutiérrez, and F. Rodríguez, Eur. J. Org. Chem., 1383 (2006).
J. S. Yadav, B. V. Subba Reddy, G. G. K. S. Narayana Kumar, and K. V. Raghavendra Rao, Chem. Lett., 36, 942 (2007).
Z.-P. Zhan, W.-Z. Yang, R.-F. Yang, J.-L. Yu, J.-P. Li, and H.-J. Liu, Chem. Commun., 3352 (2006).
Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, and S. Uemura, J. Am. Chem. Soc., 124, 11846 (2002).
H. Matsuzawa, Y. Miyake, and Y. Nishibayashi, Angew. Chem., Int. Ed., 46, 6488 (2007).
Y. Inada, M. Yoshikawa, M. D. Milton, Y. Nishibayashi, and S. Uemura, Eur. J. Org. Chem., 881 (2006).
Y. Chen, G. Li, and Y. Liu, Adv. Synth. Catal., 353, 392 (2011).
J. A. McCubbin, C. Nassar, and O. V. Krokhin, Synthesis, 3152 (2011).
This work was carried out with the financial support of the Russian Foundation for Basic Research (grant 14-03-31728 mol-a) and the Ministry of Education and Science of the Russian Federation (4.246.2014/K).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 860-875, June, 2014.
Rights and permissions
About this article
Cite this article
Uchuskin, M.G., Makarov, A.S. & Butin, A.V. Catalytic Alkylation of Furans by π-Activated Alcohols (Review). Chem Heterocycl Comp 50, 791–806 (2014). https://doi.org/10.1007/s10593-014-1534-z
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1534-z