Recent Developments in the Chemistry of Polyvalent Iodine Compounds
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1 Recent Developments in the Chemistry of Polyvalent Iodine Compounds Jiang Zhongping Content I. Introduction II. Iodine(III) Compounds III. Iodine(V) Compounds IV. Conclusions
2 Introduction Why polyvalent iodine compounds?? 1. Useful oxidizing properties 2. Environmentally benign 3. Commercial availability History Iodine Organoiodine Compounds PhICl 2 ash of seaweed 1811 the mid 1800s 1886 Williamson ether Wurtz coupling
3 Viktor V. Zhdankin University of Minnesota, Duluth. Peter J. Stang University of Utah. Iodine(III) Compounds A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides
4 A. Iodosylarenes ArIO Actual structure of PhIO A zigzag polymeric structure monomeric units PhI + -O - are linked by intermolecular I---O secondary bonds. Carmalt, C. J. et al J.Chem. Soc., Chem. Commun. 1994, 2367 Richter, H. W. et al J. Am. Chem. Soc. 1997, 119, 9614 Macikenas, D. et al J. Am. Chem. Soc. 1999, 121, 7164
5 Catalyst : Hydroxylic solvent Oxidations with PhIO Lewis acid, bromide anion, transition-metal complex Moriarty, R. M. et al Synth. Commun. 1997, 27, 3273 Hill, C. L. et al Inorg. Chem. 1983, 22, 1563 Tohma, H. et al Tetrahedron Lett. 1998, 39, 4547 Tohma, H. et al Angew. Chem., Int. Ed. 2000, 39, 1306
6 Generation of Oxygen Radicals Francisco, C. G. et al J. Org. Chem. 2001, 66,1861 Generation of Nitrogen-Centered Radicals Francisco, C. G. et al Tetrahedron: Asymmetry 2000, 11, 3879
7 Asymmetric Epoxidation Daly, A. M. et al Org. Lett. 2001, 3, 663 Hydrocarbon Hydroxylation Breslow, R. et al Tetrahedron Lett. 1998, 39, 2887
8 Transition-Metal-Catalyzed Oxygenations Adam, W. et al Org. Lett. 2000, 2, 2773 Cicchi, S. et al Tetrahedron Lett. 1999, 40, 1989 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides
9 B. Halides 1. Fluorides fluorinating reagent 4-MeC 6 H 4 IF 2 ArIF(OTf) 2. Chlorides chlorinating reagent PhICl 2 Fluorinating Reagent Greaney, M. F. et al Tetrahedron Lett. 2000, 41, 4467 Greaney, M. F. et al Tetrahedron Lett. 2000, 41, 4463
10 Greaney, M. F. et al Tetrahedron Lett. 2000, 41, 4463 Hara, S. et al J. Fluorine Chem. 1998, 87, 189 Addition of Alkene Hara, S. et al Synlett 1998, 495
11 Rearrangement Hara, S. et al Tetrahedron Lett. 1998, 39, 2589 Chlorinating Reagent Zanka, A. et al Org. Process Res. Dev. 1998, 2, 270 Ito, S. et al Synth. Commun. 1996, 26, 1441
12 Thiocyanation with PhICl 2 /Pb(SCN) 2 Prakash, O. et al Synlett 1997, 1255 Prakash, O. et al J. Org. Chem. 2001, 66, 2019 Kita, Y. et al Chem. Pharm. Bull. 1997, 45, 1887 Filippou, A. C. et al Organometallics 1999, 18, 2649
13 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides C. Carboxylates Oxidation of Alcohols Oxidative Functionalization of Alkenes Oxidative Rearrangements and Fragmentations Oxidations of Sulfur, Antimony and Bismuth Compounds Oxidative Halogenation Generation of Oxygen- and Nitrogen-Centered Radicals Oxidation of Phenols Oxidation of Phenol Ethers Cyclopropanation Radical Substitution with Azide
14 Oxidation of Alcohols De Mico, A. et al J. Org. Chem. 1997, 62, 6974 Oxidative Functionalization of Alkenes De Mico, A. et al J. Chem. Soc., Chem. Commun. 1997,
15 Tingoli, M. et al Synth. Commun. 1998, 28, 1769 Oxidative Rearrangements and Fragmentations Zhang, L.-H. et al J. Org. Chem. 1997, 62, 6918 Erdelmeier, I. et al J. Org. Chem. 2000, 65, 8152
16 Ohno, M. et al J. Org. Chem. 1999, 64, 8995 Oxidations of Sulfur, Antimony and Bismuth Compounds Xia, M. et al Synth. Commun. 1997, 27, 1321 Shi, X.-X. et al Synth. Commun. 2000, 30, 4081
17 Combes, S. et al Tetrahedron 1998, 54, 4313 Kang, S.-K. et al J. Organomet. Chem. 2000, 610, 38 Oxidative Halogenation Togo, H. et al Synlett 1998, 534 Evans, P. A. et al J. Org. Chem. 1997, 62, 5321
18 Generation of Oxygen- and Nitrogen-Centered Radicals Muraki, T. et al Tetrahedron Lett. 1996, 37, 2441 Muraki, T. et al J. Chem. Soc., Perkin Trans , 1713 Madsen, J. et al Chem.-Eur. J. 2000, 6, 1140
19 Francisco, C. G. et al Tetrahedron Lett. 1997, 38, 4141 Katohgi, M. et al Tetrahedron 1999, 55, 14885
20 Katohgi, M. et al Tetrahedron 2001, 57, 7481 Oxidation of Phenols Kato, N. et al Synthesis 1997, 625
21 Hu, Y. et al J. A. Org. Lett. 2001, 3, 1649 Kita, Y. et al J. Org. Chem. 1996, 61, 5857 Asmanidou, A. et al Molecules 2000, 5, 874 Braun, N. A. et al J. Org. Chem. 2000, 65, 4397
22 Oxidation of Phenol Ethers Takada, T. et al J. Org. Chem. 1998, 63, 7698 Cyclopropanation P. Dauban, L. et al J. Am. Chem. Soc. 2001, 123, R. P. Wurz, A. B. et al Org. Lett. 2003, 5,
23 Radical substitution with azide TMSN3 PhI(OAc) 2 Mikael bols. et al Org. Biomol. Chem., 2005, 3, A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides
24 D. Derivatives of Strong Acids ArI(OH)OSO 2 R ArI(OH)OTs (HTIB or Koser s Reagent ) Functionalization of Carbonyl Compounds Magnus, N. A. et al J. Chem. Soc., Perkin Trans , 16, 2313 Lee, J. C. et al Synth. Commun. 1999, 29, 2769 Lee, J. C. et al Synth. Commun. 2000, 30, 4271
25 Others Reagent Moriarty, R. M. et al Tetrahedron Lett. 1997, 38, 2401 De Mico, A. et al Tetrahedron 1997, 53, A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides
26 E. Azidoiodanes PhIO/TMSN 3 introduction of the azido Magnus, P. et al J. Am. Chem. Soc. 1996, 118, 3406 Magnus, P. et al Synthesis 1998, 547 Tohma, H. et al J. Chem. Soc., Chem Commun. 1998, 173
27 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides F. Benziodoxoles Ochiai, M. et al J. Am. Chem. Soc. 1996, 118, 7716 Zhdankin, V. V. et al J. Org. Chem. 1996, 61, 6547
28 Oxidize Ether to Ester Ochiai, M. et al J. Am. Chem. Soc. 1996, 118, 7716 Ochiai, M. et al J. Org. Chem. 1997, 62, 4253
29 Muraki, T. et al Synlett 1998, 286 Muraki, T. et al J. Org. Chem. 1999, 64, 2883 Zhdankin, V. V. et al J. Am. Chem. Soc. 1996, 118, 5192
30 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G.Benziodazoles I. Iodonium Salts J. Iodonium Ylides K. Iodonium Imides I. Iodonium Salts R 2 I + X - 1. Alkyl- and Fluoroalkyliodonium Salts 2. Aryl- and Heteroaryliodonium Salts 3. Alkenyliodonium Salts 4. Alkynyliodonium Salts
31 1. Alkyl- and Fluoroalkyliodonium Salts Alkylating Reagent Zhdankin, V. V. et al J. Am. Chem. Soc. 1997, 119, 4775 DesMarteau, D. D. et al J. Chem. Soc., Chem. Commun. 1998, Aryl- and Heteroaryliodonium Salts Arylating Reagent Martin-Santamaria, S. et al J. Chem. Soc., Chem. Commun. 2000, 649 Iwama, T. et al Org. Lett. 1999, 1, 673
32 Catalyzed by Transition Metals Chen, D.-W. et al J. Org. Chem. 1999, 64, 6804 Radhakrishnan, U. et al Org. Lett. 2001, 3, 859 Benzyne Precursors Kitamura, T. et al J. Am. Chem. Soc. 1999, 121, Kitamura, T. et al J. Org. Chem. 1998, 63, 8579
33 Kitamura, T. et al J. Am. Chem. Soc. 1999, 121, Okuma, K. et al Tetrahedron Lett. 1996, 37, Alkenyliodonium Salts Alkenylating Reagent Yan, J. et al Synth. Commun. 2000, 30, 3897 Ochiai, M. et al J. Org. Chem. 1997, 62, 2130
34 Cross-Coupling Reaction Hinkle, R. J. et al Org. Lett. 2000, 2, Pirguliyev, N. Sh. et al Tetrahedron 1999, 55, Alkynyliodonium Salts Alkynylating Reagent Witulski, B. et al. Angew. Chem., Int. Ed. Engl. 1999, 38, 2426 Kitamura, T. et al Tetrahedron Lett. 1998, 39, 3787
35 Cross-Coupling Reaction Kitamura, T. et al J. Am. Chem. Soc. 1997, 119, 619 Sun, A.-M. et al Tetrahedron 1999, 55, [3+2] Cycloaddition Stang, P. J. et al Tetrahedron Lett. 1997, 38, 8793
36 Diels-Alder Cycloaddition Murch, P. et al J. Org. Chem. 1997, 62, 5959 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides
37 J. Iodonium Ylides Papoutsis, I. et al Tetrahedron 1997, 53, 6097 Carbene Precursor Ochiai, M. et al J. Am. Chem. Soc. 1997, 119, Ochiai, M. et al J. Org. Chem. 1999, 64, 3181
38 Transition-Metal-Catalyzed Reaction Moriarty, R. M. et al Tetrahedron Lett. 1997, 38, 4333 Kume, M. et al Tetrahedron 1997, 53, 1635 [3+2] Cycloaddition Gogonas, E. P. et al Tetrahedron Lett. 2000, 41, 9299
39 A. Iodosylarenes B. Halides C. Carboxylates D. Derivatives of Strong Acids E. Azidoiodanes F. Benziodoxoles G. Benziodazoles H. Iodonium Salts I. Iodonium Ylides J. Iodonium Imides K. Iodonium Imides Transition-Metal-Catalyzed Aziridination of Olefins ArI=NSO 2 R Nitrene Precursor Dauban, P. et al Tetrahedron Lett. 1998, 39, 5739 Di Chenna, P. H. et al Tetrahedron Lett. 2000, 41, 7041
40 Transition-Metal-Catalyzed C- H Amidation Yang, J. et al J. Chem. Soc., Chem. Commun. 2000, 531 Zhou, X.-G. et al J. Chem. Soc., Chem. Commun. 1999, 2377 III. Iodine(V) Compounds A. Organic Iodyl Compounds B. Benziodoxole Oxides C. Dess-Martin Periodinane
41 A. Organic Iodyl Compounds ArIO 2 Kazmierczak, P. et al Molecules 2001, 6, 881 Tohma, H. et al J. Org. Chem. 1999, 64, 3519 B. Benziodoxole Oxides IBX Frigerio, M. et al J. Org. Chem. 1999, 64, 4537 Paintner, F. F. et al Synthesis 2001, 2113
42 S. Kotha, S. et al Synlett 2004, Maiti, A. et al Synth. Commun. 2001, 31, 1499 Nicolaou, K. C. et al J. Am. Chem. Soc. 2000, 122, 7596 Nicolaou, K. C. et al J. Am. Chem. Soc. 2001, 123, 3183
43 K. C. Nicolaou. et al J. Am. Chem. Soc. 2004, 126, K. C. Nicolaou. et al J. Am. Chem. Soc. ASAP
44 C. Dess-Martin Periodinane Lawrence, N. J. et al Tetrahedron Lett. 2001, 42, 3939 Yu, C. et al Tetrahedron Lett. 2001, 42, 5167 Rocaboy, C. et al Eur. J. Org. Chem. 2000, 2621 Roels, J. et al Synlett 2001, 789
45 Barrett, A. G. M. et al J. Org. Chem. 1997, 62, 9376 Chaudhari, S. S. et al Synthesis 1999, 760 IV. Conclusions Commercial Availability Oxidizing Properties Environmentally Benign The use of the polymer supported polyvalent iodine reagents The transition-metal-catalyzed coupling reactions of iodonium
46 Acknowledgment Prof. Gan Prof. Shi and Prof. Yu Thanks for your attention!
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