Hypervalent Iodine Compounds in Carbohydrate Chemistry: Glycosylation, Functionalization and Oxidation.

Anomeric Arylation Glycosylaion Hypervalent Iodinium Compounds (HIC) Photoinduced

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
13 Feb 2024
Historique:
received: 08 01 2024
pubmed: 13 2 2024
medline: 13 2 2024
entrez: 13 2 2024
Statut: aheadofprint

Résumé

This mini review article provides an overview on the use of hypervalent iodine compounds (HICs) in carbohydrate synthesis, focusing on their chemistry and recent applications. HICs are similar to transition metals in their reactivity but have the added benefit of being environmentally benign, and are therefore commonly used as selective oxidants and eco-friendly reagents in organic synthesis. Herein, we summarize various synthetic uses of hypervalent iodine reagents in reactions such as glycosylation, oxidations, functionalization, and C-C bond-forming reactions. The goal of this review is to illustrate the advantages and versatility of using HICs as an environmentally sustainable alternative to heavy metals in carbohydrate chemistry.

Identifiants

pubmed: 38349955
doi: 10.1002/chem.202400087
doi:

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202400087

Subventions

Organisme : Engineering and Physical Sciences Research Council
ID : EP/T020288/1 and EP/S026215/1
Organisme : Knut och Alice Wallenbergs Stiftelse
ID : 2019.0071
Organisme : Swedish Research Council

Informations de copyright

© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Références

A. Yoshimura, V. V. Zhdankin, Chem. Rev. 2016, 116, 3328-3435.
C. Hartmann, V. Meyer, Ber. Dtsch. Chem. Ges. 2006, 27, 426-432.
 
V. V. Zhdankin, Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Application of Polyvalent Iodine Compounds John Wiley & Sons Ltd.: New York, 2014;
T. Kaiho, Iodine Ed. Chemistry and Applications, John Wiley & Sons, Inc.: New York, 2-15;
T. Wirth, IodineEd. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis., Vol. 224, Top. Curr. Chem., 2003;
A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH Publishers, Inc.: New York, 1992; eA. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press: London, 1997.
 
V. V. S. Zhdankin, P. J. (Ed.: K. y. Akiba, Ed.), VCH Publishers: New York, 1999;
K. y. Akiba, Ed.; Wiley-VCH: New York, 1999;
M. Ochiai, (Ed.: K. y. Akiba), VCH Publishers: New York, 1999;
D. D. Holsworth (Ed.: J. J. Li, Corey, E. J.), John Wiley & Sons, Inc.: Hoboken, NJ, 2007;
H.-J. Frohn, John Wiley & Sons, Inc.: New York, 2012.
 
P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178;
V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584;
V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299-5358;
P. J. Stang, J. Org. Chem. 2003, 68, 2997-3008;
R. M. Moriarty, J. Org. Chem. 2005, 70, 2893-2903;
V. V. Zhdankin, J. Org. Chem. 2011, 76, 1185-1197;
V. V. Zhdankin, V. V. Zhdankin, Arkivoc 2009, 2009, 1-62;
S. Y. Mekhman, V. Z. Viktor, Curr. Org. Synth. 2012, 9, 247-272;
T. Wirth, Synthesis 1999, 1999, 1271-1287;
T. Wirth, Angew. Chem. Int. Ed. 2005, 44, 3656-3665;
E. D. Matveeva, M. V. Proskurnina, N. S. Zefirov, Heteroat. Chem. 2006, 17, 595-617;
T. Kitamura, Y. Fujiwara, Chem. Informationsdienst 2010, 28, 0931-7597;
A. Varvoglis, Tetrahedron 1997, 53, 1179-1255;
L. Skulski, Molecules 2000, 5, 1331-1371;
K. Zhao, J. Sun, D. Zhang-Negrerie, Y. Du, Reports in Organic Chemistry 2016, 6, 25-45.
 
E. A. Merritt, B. Olofsson, Angew. Chem. Int. Ed. 2009, 48, 9052-9070;
R. M. White, M. A. Battiste, J. Org. Chem. 1976, 41, 1245-1248;
J. P. Brand, J. Waser, Chem. Soc. Rev. 2012, 41, 4165-4179;
E. A. Merritt, B. Olofsson, Synthesis 2011, 2011, 517-538;
V. V. Grushin, Chem. Soc. Rev. 2000, 29, 315-324;
T. Umemoto, Chem. Rev. 1996, 96, 1757-1778;
P. Muller, Acc. Chem. Res. 2004, 37, 243-251;
J. P. Brand, D. Fernandez Gonzalez, S. Nicolai, J. Waser, Chem. Commun. 2011, 47, 102-115;
T. Patonay, K. Konya, E. Juhasz-Toth, Chem. Soc. Rev. 2011, 40, 2797-2847;
M. Ochiai, Coord. Chem. Rev. 2006, 250, 2771-2781;
V. V. Zhdankin, J. D. Protasiewicz, Coord. Chem. Rev. 2014, 275, 54-62;
M. Ciufolini, N. Braun, S. Canesi, M. Ousmer, J. Chang, D. Chai, Synthesis 2007, 2007, 3759-3772;
D. Magdziak, S. J. Meek, T. R. Pettus, Chem. Rev. 2004, 104, 1383-1430;
I. Moreno, I. Tellitu, M. Herrero, R. SanMartin, E. Dominguez, Curr. Org. Chem. 2002, 6, 1433-1452;
L. F. Silva Jr., Molecules 2006, 11, 421-434;
T. Dohi, Y. Kita, ChemCatChem 2014, 6, 76-78;
N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924-1935;
T. Wirth, M. Brown, U. Farid, Synlett 2013, 24, 424-431;
H. Liang, M. A. Ciufolini, Angew. Chem. Int. Ed. 2011, 50, 11849-11851;
A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354-362;
T. Dohi, N. Takenaga, T. Nakae, Y. Toyoda, M. Yamasaki, M. Shiro, H. Fujioka, A. Maruyama, Y. Kita, J. Am. Chem. Soc. 2013, 135, 4558-4566;
T. Dohi, Y. Kita, Chem. Commun. 2009, 2073-2085;
R. D. Richardson, T. Wirth, Angew. Chem. Int. Ed. 2006, 45, 4402-4404;
Y. Yoshimura, H. Wakamatsu, Y. Natori, Y. Saito, N. Minakawa, Beilstein J. Org. Chem. 2018, 14, 1595-1618,
K. B. Pal, E. M. Di Tomasso, A. K. Inge, B. Olofsson, Angew. Chem. Int. Ed. 2023, 62, e202301368.
 
S. Spyroudis, E. Malamidou-Xenikaki, Synlett 2008, 2008, 2725-2740;
W. Kirmse, Eur. J. Org. Chem. 2005, 2005, 237-260.
H.-J. Frohn, M. E. Hirschberg, A. Wenda, V. V. Bardin, J.Fluor. Chem. 2008, 129, 459-473.
H. Togo, K. Sakuratani, Synlett 2002, 1966-1975.
 
V. V. Zhdankin, C. D. Turner, M. A. Ciufolini, Arkivoc 2011, 2011, 410-428;
L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235-2261;
Y. Kita, H. Fujioka, Pure Appl. Chem. 2007, 79, 701-713;
S. Quideau, L. Pouysegu, D. Deffieux, Curr. Org. Chem. 2004, 8, 113-148.
H. Morales-Rojas, R. A. Moss, Chem. Rev. 2002, 102, 2497-2521.
A. Duschek, S. F. Kirsch, Angew. Chem. Int. Ed. 2011, 50, 1524-1552.
X. Xiao, J. M. Roth, N. S. Greenwood, M. K. Velopolcek, J. Aguirre, M. Jalali, A. Ariafard, S. E. Wengryniuk, J. Org. Chem. 2021, 86, 6566-6576.
S. E. Shetgaonkar, F. V. Singh, Org. Biomol. Chem. 2023, 21, 4163-4180.
V. V. Zhdankin, M. S. Yusubov, A. V. Maskaev, V. V. Zhdankin, Arkivoc 2011, 2011, 370-409.
 
T. Y. R. Tsai, H. Jin, K. Wiesner, Can. J. Chem. 1984, 62, 1403-1405;
P. J. Garegg, C. Henrichson, T. Norberg, Carbohydr. Res. 1983, 116, 162-165;
J. W. Van Cleve, Carbohydr. Res. 1979, 70, 161-164.
 
T. Mukaiyama, T. Nakatsuka, S.-i. Shoda, Chem. Lett. 1979, 8, 487-490;
S. Sato, M. Mori, Y. Ito, t. Ogawa, Carbohydr. Res. 1986, 155, C6-C10.
G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331-1334.
 
G. Lian, X. Zhang, B. Yu, Carbohydr. Res. 2015, 403, 13-22;
S. Escopy, A. V. Demchenko, Chemistry 2022, 28, e202103747.
K. Fukase, A. Hasuoka, I. Kinoshita, S. Kusumoto, Tetrahedron Lett. 1992, 33, 7165-7168.
K. Fukase, I. Kinoshita, T. Kanoh, Y. Nakai, A. Hasuoka, S. Kusumoto, Tetrahedron 1996, 52, 3897-3904.
T. Kajimoto, K. Morimoto, R. Ogawa, T. Dohi, Y. Kita, Eur. J. Org. Chem. 2015, 2015, 2138-2142.
A. H. Chu, A. Minciunescu, V. Montanari, K. Kumar, C. S. Bennett, Org. Lett. 2014, 16, 1780-1782.
C. S. Bennett, M. C. Galan, Chem. Rev. 2018, 118, 7931-7985.
A. H. Chu, A. Minciunescu, C. S. Bennett, Org. Lett. 2015, 17, 6262-6265.
R. C. Saliba, Z. J. Wooke, G. A. Nieves, A. A. Chu, C. S. Bennett, N. L. B. Pohl, Org. Lett. 2018, 20, 800-803.
K. Morimoto, K. Yanase, T. Kajimoto, Y. Kita, Org. Lett. 2022, 24, 9028-9032.
A. Sau, C. Palo-Nieto, M. C. Galan, J. Org. Chem. 2019, 84, 2415-2424.
T. Kurz, K. Morimoto, Y. Kita, T. Kajimoto, Arkivoc 2021, 2021, 164-176.
 
S. K. Mamidyala, M. G. Finn, J. Org. Chem. 2009, 74, 8417-8420;
Y. Du, G. Gu, G. Wei, Y. Hua, R. J. Linhardt, Org. Lett. 2003, 5, 3627-3630.
T. Yang, F. Zhu, M. A. Walczak, Nat. Commun. 2018, 9, 3650.
P. G. Hultin, Curr. Top. Med. Chem. 2005, 5, 1299-1331.
 
A. C. Drohat, A. Maiti, Org. Biomol. Chem. 2014, 12, 8367-8378;
R. Wolfenden, X. Lu, G. Young, J. Am. Chem. Soc. 1998, 120, 6814-6815.
 
J. Ramnauth, O. Poulin, S. Rakhit, S. P. Maddaford, Org. Lett. 2001, 3, 2013-2015;
D. C. Xiong, L. H. Zhang, X. S. Ye, Org. Lett. 2009, 11, 1709-1712;
C. F. Liu, D. C. Xiong, X. S. Ye, J. Org. Chem. 2014, 79, 4676-4686.
S. Xiang, S. Cai, J. Zeng, X. W. Liu, Org. Lett. 2011, 13, 4608-4611.
Y. Bai, M. H. Kim le, H. Liao, X. W. Liu, J. Org. Chem. 2013, 78, 8821-8825.
A. K. Kusunuru, S. K. Yousuf, M. Tatina, D. Mukherjee, Eur. J. Org. Chem. 2015, 2015, 459-462.
J. Ma, S. Xiang, H. Jiang, X.-W. Liu, Eur. J. Org. Chem. 2015, 2015, 949-952.
H. H. Li, X. S. Ye, Org. Biomol. Chem. 2009, 7, 3855-3861.
A. K. Singh, J. Kandasamy, Org. Biomol. Chem. 2018, 16, 5107-5112.
D. P. Steinhuebel, J. J. Fleming, J. Du Bois, Org. Lett. 2002, 4, 293-295.
D. Yi, F. Zhu, M. A. Walczak, Org. Lett. 2018, 20, 1936-1940.
K. B. Pal, J. Lee, M. Das, X. W. Liu, Org. Biomol. Chem. 2020, 18, 2242-2251.
L. Shi, Y. J. Kim, D. Y. Gin, J. Am. Chem. Soc. 2001, 123, 6939-6940.
M. Islam, N. D. Tirukoti, S. Nandi, S. Hotha, J. Org. Chem. 2014, 79, 4470-4476.
A. Kirschning, C. Plumeier, L. Rose, Chem. Commun. 1998, 33-34.
J. E. Leffler, L. J. Story, J. Am. Chem. Soc. 2002, 89, 2333-2338.
A. Kirschning, M. A. Hashem, H. Monenschein, L. Rose, K.-U. Schöning, J. Org. Chem. 1999, 64, 6522-6526.
 
D. Van Ende, A. Krief, Angew. Chem. Int. Ed. 1974, 13, 279-279;
G. A. Olah, Q. Wang, X.-Y. Li, G. K. Surya Prakash, Synlett 1990, 1990, 487-489;
A. Hassner, F. Boerwinkle, J. Am. Chem. Soc. 2002, 90, 216-218.
A. Kirschning, M. Jesberger, H. Monenschein, Tetrahedron Lett. 1999, 40, 8999-9002.
M. Tingoli, M. Tiecco, D. Chianelli, R. Balducci, A. Temperini, J. Org. Chem. 2002, 56, 6809-6813.
M. Tiecco, L. Testaferri, M. Tingoli, D. Bartoli, J. Org. Chem. 2002, 55, 4523-4528.
M. Tingoli, M. Tiecco, L. Testaferri, A. Temperini, J. Chem. Soc. Chem. Commun. 1994.
K. Lu, Y. Ma, S. Liu, S. Guo, Y. Zhang, Chin. J. Chem. 2022, 40, 681-686.
A. S. Henderson, S. Medina, J. F. Bower, M. C. Galan, Org. Lett. 2015, 17, 4846-4849.
V. Dimakos, M. S. Taylor, Org. Biomol. Chem. 2021, 19, 514-524.
G. L. Tolnai, U. J. Nilsson, B. Olofsson, Angew. Chem. Int. Ed. 2016, 55, 11226-11230.
G. Kervefors, K. B. Pal, G. L. Tolnai, M. Mahanti, H. Leffler, U. J. Nilsson, B. Olofsson, Helv. Chim. Acta 2021, 104.
N. Lucchetti, R. Gilmour, Chem. Eur. J. 2018, 24, 16266-16270.
A. Axer, S. Hermann, G. Kehr, D. Clases, U. Karst, L. Fischer-Riepe, J. Roth, M. Fobker, M. Schafers, R. Gilmour, A. Faust, ChemMedChem 2018, 13, 241-250.
W. Shang, Z. D. Mou, H. Tang, X. Zhang, J. Liu, Z. Fu, D. Niu, Angew. Chem. Int. Ed. 2018, 57, 314-318.
S. De Munari, M. Frigerio, M. Santagostino, J. Org. Chem. 1996, 61, 9272-9279.
A. Kirschning, J. Org. Chem. 2002, 60, 1228-1232.
A. Chennaiah, A. K. Verma, Y. D. Vankar, J. Org. Chem. 2018, 83, 10535-10540.
M. Yadav, C. L. Liotta, R. Krishnamurthy, Bioorg. Med. Chem. Lett. 2018, 28, 2759-2765.

Auteurs

Mukul Mahanti (M)

School of Chemistry, University of Bristol Cantock's Close, BS81TS, Bristol, United Kingdom.

Kumar Bhaskar Pal (K)

Department of Chemistry and Molecular Biology, University of Gothenburg, Medicinaregatan 7B, 413 90, Gothenburg, Sweden.

Carl Johan Wallentin (CJ)

Department of Chemistry and Molecular Biology, University of Gothenburg, Medicinaregatan 7B, 413 90, Gothenburg, Sweden.

M Carmen Galan (MC)

School of Chemistry, University of Bristol Cantock's Close, BS81TS, Bristol, United Kingdom.

Classifications MeSH