Abstract
Organotellurium compounds serve as excellent precursors for carbon-centered radicals,
which have significant synthetic utility ranging from the formation of highly functionalized
small molecules to structurally well-defined macromolecules. This review focuses on
the radical reactions of organotellurium compounds, with an emphasis on the new carbon-carbon
bond formation reaction developed in the author’s laboratory.
1 Introduction
2 Reversible Radical Generation from Organotellurium Compounds
3 Radical Addition to Unsaturated Carbon-Carbon Bonds
3.1 Glycosyl Radical Addition to Alkynes
3.2 Functionalization of Quinones
3.3 Group-Transfer Imidoylation of Isonitriles
4 Silyltelluride-Mediated Radical Coupling Reactions
4.1 Coupling of Carbonyl Compounds with Isonitriles
4.2 Coupling of Carbonyl Compounds with Alkynes
4.3 Coupling of Imines with Isonitriles
4.4 Reductive bis-Silylation of Quinones
5 Living Radical Polymerization
5.1 Development of New Initiators
5.2 Confirmation of Living Character
5.3 Selective Modification of Polymer-End Group
5.4 Development of High-Speed TERP
6 Summary
References
<A NAME="RA34504ST-1A">1a </A>
Radicals in Organic Synthesis
Renaud P.
Sibi M.
Wiley-VCH;
Weinheim:
2001.
<A NAME="RA34504ST-1B">1b </A>
Curran D.
Porter NA.
Giese B.
Stereochemistry of Radical Reactions
VCH;
Weinheim:
1995.
<A NAME="RA34504ST-1C">1c </A>
Curran D. In
Comprehensive Organic Synthesis
Vol 4:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.715-831
<A NAME="RA34504ST-1D">1d </A>
Giese B.
Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds
Pergamon Press;
Oxford:
1986.
<A NAME="RA34504ST-2A">2a </A>
Fisher H.
Chem. Rev.
2001,
101:
3581
<A NAME="RA34504ST-2B">2b </A>
Studer A.
Chem.-Eur. J.
2001,
7:
1159
<A NAME="RA34504ST-3A">3a </A>
Curran DP.
Martin-Esker AA.
Ko S.-B.
Newcomb M.
J. Org. Chem.
1993,
58:
4691
<A NAME="RA34504ST-3B">3b </A>
Newcomb M.
Tetrahedron
1993,
49:
1151
<A NAME="RA34504ST-3C">3c </A>
Russell GA.
Tashtoush H.
J. Am. Chem. Soc.
1983,
105:
1398
<A NAME="RA34504ST-4">4 </A>
Clive DLJ.
Chittattu GJ.
Farina V.
Kiel W.
Menchen SM.
Russell CG.
Singh A.
Wong CK.
Curtis N.
J. Am. Chem. Soc.
1980,
102:
4438
<A NAME="RA34504ST-5A">5a </A>
Barton DHR.
Ozbalik N.
Sarma JC.
Tetrahedron Lett.
1988,
29:
6581
<A NAME="RA34504ST-5B">5b </A>
Barton DHR.
Ramesh M.
J. Am. Chem. Soc.
1990,
112:
891
<A NAME="RA34504ST-5C">5c </A>
Barton DHR.
Géro SD.
Quiclet-Sire B.
Samadi M.
Vincent C.
Tetrahedron
1991,
47:
9383
<A NAME="RA34504ST-5D">5d </A>
Barton DHR.
Dalko P.
Géro SD.
Tetrahedron Lett.
1991,
32:
4713
<A NAME="RA34504ST-6A">6a </A>
Han L.-B.
Ishihara K.
Kambe N.
Ogawa A.
Ryu I.
Sonoda N.
J. Am. Chem. Soc.
1992,
114:
7591
<A NAME="RA34504ST-6B">6b </A>
Han L.-B.
Ishihara K.
Kambe N.
Ogawa A.
Sonoda N.
Phosphorous, Sulfur Silicon Rel. Elem.
1992,
67:
243
<A NAME="RA34504ST-7A">7a </A>
Chen C.
Crich D.
Papadatos A.
J. Am. Chem. Soc.
1992,
114:
8313
<A NAME="RA34504ST-7B">7b </A>
Crich D.
Chen C.
Hwang J.-T.
Yuan H.
Papadatos A.
Walter RI.
J. Am. Chem. Soc.
1994,
116:
8937
<A NAME="RA34504ST-8A">8a </A>
Engman L.
Gupta V.
J. Chem. Soc., Chem. Commun.
1995,
2515
<A NAME="RA34504ST-8B">8b </A>
Engman L.
Gupta V.
J. Org. Chem.
1997,
62:
157
<A NAME="RA34504ST-8C">8c </A>
Berlin S.
Ericsson C.
Engman L.
Org. Lett.
2002,
4:
1
<A NAME="RA34504ST-9A">9a </A>
Lucas MA.
Schiesser CH.
J. Org. Chem.
1996,
61:
5754
<A NAME="RA34504ST-9B">9b </A>
Lucas MA.
Schiesser CH.
J. Org. Chem.
1998,
63:
3032
<A NAME="RA34504ST-10A">10a </A>
Yamago S.
Kokubo K.
Yoshida J.
Chem. Lett.
1997,
111
<A NAME="RA34504ST-10B">10b </A>
Yamago S.
Kokubo K.
Hara O.
Masuda S.
Yoshida J.
J. Org. Chem.
2002,
67:
8584
<A NAME="RA34504ST-11">11 </A>
Yamago S.
Kokubo K.
Masuda S.
Yoshida J.
Synlett
1996,
929
<A NAME="RA34504ST-12A">12a </A>
Yamago S.
Nakamura E.
Org. React.
2002,
61:
1
<A NAME="RA34504ST-12B">12b </A>
Nakamura E.
Yamago S.
Acc. Chem. Res.
2002,
35:
867
<A NAME="RA34504ST-13">13 </A>
Yamago S.
Miyazoe H.
Yoshida J.
Tetrahedron Lett.
1999,
40:
2339
<A NAME="RA34504ST-14">14 </A>
Miyazoe H.
Yamago S.
Yoshida J.
Angew. Chem. Int. Ed.
2000,
39:
3669
<A NAME="RA34504ST-15">15 </A>
Goto A.
Kwak Y.
Fukuda T.
Yamago S.
Iida K.
Nakajima M.
Yoshida J.
J. Am. Chem. Soc.
2003,
125:
8720
<A NAME="RA34504ST-16">16 </A>
Yamago S.
Miyazoe H.
Yoshida J.
Tetrahedron Lett.
1999,
40:
2343
<A NAME="RA34504ST-17A">17a </A>
Postema MHD.
C-Glycoside Synthesis
CRC Press;
Boca Raton:
1995.
<A NAME="RA34504ST-17B">17b </A>
Giese B.
Zeitz H.-G. In
Comprehensive Carbohydrate Chemistry
Hanessian S.
Marcel Dekker;
New York:
1997.
p.507
<A NAME="RA34504ST-17C">17c </A>
Skrkdstrup T.
Vauzeilles B.
Beau J.-M. In Carbohydrates in Chemistry and Biology
Vol. 1:
Ernst B.
Hart GW.
Sinaӱ P.
Wiley-VCH;
Weinheim:
2000.
p.495
<A NAME="RA34504ST-17D">17d </A>
Pearce AJ.
Mallet J.-M.
Sinaӱ P. In Radicals in Organic Synthesis
Vol. 2:
Renaud P.
Sibi MP.
Wiley-VCH;
Weinheim:
2001.
p.538
<A NAME="RA34504ST-17E">17e </A>
Yamago S.
Yoshida J. In CRC Handbook of Organic Photochemistry and Photobiology
2nd ed., Vol. 2-1:
Horspool W.
Lenci F.
CRC Press;
Boca Raton:
2004.
<A NAME="RA34504ST-17F">17f </A>
Togo H.
He W.
Waki Y.
Yokoyama M.
Synlett
1998,
700
<A NAME="RA34504ST-18">18 </A>
Araki Y.
Endo T.
Tanji M.
Nagasawa J.
Ishido Y.
Tetrahedron Lett.
1987,
28:
5853
<A NAME="RA34504ST-19A">19a </A>
Giese B.
Dupuis J.
Tetrahedron Lett.
1984,
25:
1349
<A NAME="RA34504ST-19B">19b </A>
Descotes G.
J. Carbohydr. Chem.
1988,
7:
1
<A NAME="RA34504ST-20A">20a </A>
Yamago S.
Hashidume M.
Yoshida J.
Chem. Lett.
2000,
1234
<A NAME="RA34504ST-20B">20b </A>
Yamago S.
Hashidume M.
Yoshida J.
Tetrahedron
2002,
58:
6805
<A NAME="RA34504ST-21A">21a </A>
Naruta Y.
Maruyama K.
The Chemistry of the Quinonoid Compounds
Vol. 2:
Patai S.
Rappoport Z.
Wiley;
New York:
1988.
Chap. 8.
<A NAME="RA34504ST-21B">21b </A>
Naruta Y.
Maruyama K.
J. Synth. Org. Chem. Jpn.
1984,
42:
415
<A NAME="RA34504ST-21C">21c </A>
Fukuyama T.
J. Synth. Org. Chem. Jpn.
1988,
46:
801
<A NAME="RA34504ST-21D">21d </A>
Owton WM.
J. Chem. Soc., Perkin Trans. 1
1999,
2409
<A NAME="RA34504ST-22A">22a </A>
Huyser ES.
Amini B.
J. Org. Chem.
1968,
33:
576
<A NAME="RA34504ST-22B">22b </A>
Jacobsen N.
Torssell K.
Liebigs Ann. Chem.
1972,
763:
135
<A NAME="RA34504ST-22C">22c </A>
Citterio A.
Vismara E.
Bernardi R.
J. Chem. Res., Synop.
1983,
88
<A NAME="RA34504ST-22D">22d </A>
Barton DHR.
Bridon D.
Zard SZ.
Tetrahedron
1987,
43:
5307
<A NAME="RA34504ST-22E">22e </A>
Barton DHR.
Sas W.
Tetrahedron
1990,
46:
3419
<A NAME="RA34504ST-22F">22f </A>
Coppa F.
Fontana F.
Lazzarini E.
Minisci F.
Chem. Lett.
1992,
1299
<A NAME="RA34504ST-22G">22g </A>
Kraus GA.
Kirihara M.
J. Org. Chem.
1992,
57:
3256
<A NAME="RA34504ST-22H">22h </A>
Kraus GA.
Liu P.
Tetrahedron Lett.
1994,
35:
7723
<A NAME="RA34504ST-22I">22i </A>
Kraus GA.
Melekhov A.
Tetrahedron Lett.
1998,
39:
3957
<A NAME="RA34504ST-22J">22j </A>
Bieber LW.
Neto PJR.
Generino RM.
Tetrahedron Lett.
1999,
40:
4473
<A NAME="RA34504ST-23">23 </A>
Klingler RJ.
Mochida K.
Kochi JK.
J. Am. Chem. Soc.
1979,
101:
6626
<A NAME="RA34504ST-24">24 </A>
Ling T.
Poupon E.
Rueden EJ.
Kim SH.
Theodorakis EA.
J. Am. Chem. Soc.
2002,
124:
12261
<A NAME="RA34504ST-25">25 </A>
Sharma PK.
Khanna RN.
Monatsh. Chem.
1985,
116:
353
<A NAME="RA34504ST-26A">26a </A>
Yamago S.
Miyazoe H.
Goto R.
Yoshida J.
Tetrahedron Lett.
1999,
40:
2347
<A NAME="RA34504ST-26B">26b </A>
Yamago S.
Miyazoe H.
Sawazaki T.
Goto R.
Yoshida J.
Tetrahedron Lett.
2000,
41:
7517
<A NAME="RA34504ST-26C">26c </A>
Yamago S.
Miyazoe H.
Goto R.
Hashidume M.
Sawazaki T.
Yoshida J.
J. Am. Chem. Soc.
2001,
123:
3697
<A NAME="RA34504ST-27A">27a </A>
Ryu I.
Sonoda N.
Angew. Chem., Int. Ed. Engl.
1996,
35:
1050
<A NAME="RA34504ST-27B">27b </A>
Ryu I.
Sonoda N.
Curran DP.
Chem. Rev.
1996,
96:
177
<A NAME="RA34504ST-27C">27c </A>
Ryu I.
Chem. Soc. Rev.
2001,
30:
16
<A NAME="RA34504ST-28A">28a </A>
Saegusa T.
Ito Y.
In Isonitrile
Ugi I.
Academic Press;
New York:
1971.
p.65-92
<A NAME="RA34504ST-28B">28b </A>
Ito Y.
Murakami M.
J. Synth. Org. Chem. Jpn.
1991,
41:
184
<A NAME="RA34504ST-28C">28c </A>
Durfee LD.
Rothwell IP.
Chem. Rev.
1988,
88:
1059
<A NAME="RA34504ST-28D">28d </A>
Drenth W.
Nolte RJM.
Acc. Chem. Res.
1979,
12:
30
<A NAME="RA34504ST-29A">29a </A>
Stork G.
Sher PM.
J. Am. Chem. Soc.
1983,
105:
6765
<A NAME="RA34504ST-29B">29b </A>
Stork G.
Sher PM.
Chen H.-L.
J. Am. Chem. Soc.
1986,
108:
6384
<A NAME="RA34504ST-29C">29c </A>
Barton DHR.
Ozbalik N.
Vacher B.
Tetrahedron
1988,
44:
3501
<A NAME="RA34504ST-29D">29d </A>
Curran DP.
Liu H.
J. Am. Chem. Soc.
1991,
113:
2127
<A NAME="RA34504ST-29E">29e </A>
Curran DP.
Liu H.
Josien H.
Ko S.-B.
Tetrahedron
1996,
52:
11385
<A NAME="RA34504ST-29F">29f </A>
Josien H.
Curran DP.
Tetrahedron
1997,
53:
8881
<A NAME="RA34504ST-29G">29g </A>
Josien H.
Ko S.-B.
Bom D.
Curran DP.
Chem.-Eur. J.
1998,
4:
67
<A NAME="RA34504ST-29H">29h </A>
Luo Z.
Zhang Q.
Oderaotoshi Y.
Curran DP.
Science
2001,
291:
1766
<A NAME="RA34504ST-29I">29i </A>
Fukuyama T.
Cheng X.
Peng G.
J. Am. Chem. Soc.
1994,
116:
3127
<A NAME="RA34504ST-29J">29j </A>
Nanni D.
Pareschi P.
Rizzoli C.
Sgarabotto P.
Tundo A.
Tetrahedron
1995,
51:
9045
<A NAME="RA34504ST-29K">29k </A>
Nanni D.
Pareschi P.
Tundo A.
Tetrahedron Lett.
1996,
37:
9337
<A NAME="RA34504ST-29L">29l </A>
Camaggi CM.
Leardini R.
Nanni D.
Zanardi G.
Tetrahedron
1998,
54:
5587
<A NAME="RA34504ST-29M">29m </A>
Shinada T.
Miyachi M.
Itagaki Y.
Haoki H.
Yoshihara K.
Nakajima T.
Tetrahedron Lett.
1996,
37:
7099
<A NAME="RA34504ST-29N">29n </A>
Martin J.
Jaramillo GLM.
Wang PG.
Tetrahedron Lett.
1998,
39:
5927
<A NAME="RA34504ST-29O">29o </A>
Rainier JD.
Kennedy AR.
Chase E.
Tetrahedron Lett.
1999,
40:
6325
<A NAME="RA34504ST-29P">29p </A>
Leardini R.
Nanni D.
Zanardi G.
J. Org. Chem.
2000,
65:
2763
<A NAME="RA34504ST-30">30 </A>
Tordeux M.
Wakselman C.
Tetrahedron
1981,
37:
315
<A NAME="RA34504ST-31A">31a </A>
Lunazzi L.
Ingold KU.
Scaiano JC.
J. Phys. Chem.
1983,
87:
529
<A NAME="RA34504ST-31B">31b </A>
Turro NJ.
Gould IR.
Baretz BH.
J. Phys. Chem.
1983,
87:
531
<A NAME="RA34504ST-32A">32a </A>
Brubaker MM.
Coffman DD.
Hoehn HH.
J. Am. Chem. Soc.
1952,
74:
1509
<A NAME="RA34504ST-32B">32b </A>
Coffman DD.
Pinkney PS.
Wall FT.
Wood WH.
Young JS.
J. Am. Chem. Soc.
1952,
74:
3391
<A NAME="RA34504ST-33">33 </A>
Fischer H.
Paul H.
Acc. Chem. Res.
1987,
20:
200
<A NAME="RA34504ST-34">34 </A>
Yamago, S.; Miyazoe, H.; Yoshida, J. unpublished results.
<A NAME="RA34504ST-35">35 </A>
Chatgilialoglu C.
Chem. Rev.
1995,
95:
1229
<A NAME="RA34504ST-36A">36a </A>
Kim S.
Yoon J.-Y. In Radicals in Organic Synthesis
Vol. 2:
Renaud P.
Sibi M.
Wiley-VCH;
Weinheim:
2001.
p.1
<A NAME="RA34504ST-36B">36b </A>
Friestad GK.
Tetrahedron
2001,
57:
5461
<A NAME="RA34504ST-36C">36c </A>
Fallis AG.
Brinza IM.
Tetrahedron
1997,
53:
17543
<A NAME="RA34504ST-37A">37a </A>
Drake JE.
Hemmings RT.
Inorg. Chem.
1980,
19:
1897
<A NAME="RA34504ST-37B">37b </A>
Ohira N.
Aso Y.
Tsubo T.
Ogura F.
Chem. Lett.
1984,
853
<A NAME="RA34504ST-37C">37c </A>
Nakagawa K.
Osuka M.
Sasaki K.
Aso A.
Otsubo T.
Ogura F.
Chem. Lett.
1987,
1331
<A NAME="RA34504ST-37D">37d </A>
Sasaki K.
Aso Y.
Otsubo T.
Ogura F.
Tetrahedron Lett.
1985,
26:
453
<A NAME="RA34504ST-37E">37e </A>
Sasaki K.
Aso Y.
Otsubo T.
Ogura F.
Chem. Lett.
1986,
977
<A NAME="RA34504ST-37F">37f </A>
Schiesser CH.
Skidmore M.
J. Organomet. Chem.
1998,
552:
145
<A NAME="RA34504ST-37G">37g </A>
Zhang S.
Zhang Y.
Heteroat. Chem.
1999,
10:
471
<A NAME="RA34504ST-38">38 </A>
Chatgilialoglu C.
Ingold KU.
Scaiano JC.
J. Am. Chem. Soc.
1982,
104:
5119
<A NAME="RA34504ST-39">39 </A>
Chatgilialoglu C.
Ingold KU.
Scaiano JC.
J. Am. Chem. Soc.
1983,
105:
3292
<A NAME="RA34504ST-40">40 </A>
Newcomb M.
Tetrahedron
1993,
49:
1151
<A NAME="RA34504ST-41">41 </A>
Yamago S.
Miyoshi M.
Miyazoe H.
Yoshida J.
Angew. Chem. Int. Ed.
2002,
41:
1407
<A NAME="RA34504ST-42A">42a </A>
Galli C.
Guarnieri A.
Koch H.
Mencarelli P.
Rappoport Z.
J. Org. Chem.
1997,
62:
4072
<A NAME="RA34504ST-42B">42b </A> See also:
Miura K.
Oshima K.
Utimoto K.
Bull. Chem. Soc. Jpn.
1993,
66:
2356
<A NAME="RA34504ST-43">43 </A>
Yamago S.
Miyazoe H.
Nakayama T.
Miyoshi M.
Yoshida J.
Angew. Chem. Int. Ed.
2003,
42:
117
<A NAME="RA34504ST-44">44 </A>
Yamago S.
Miyazoe H.
Iida K.
Yoshida J.
Org. Lett.
2000,
2:
3671
<A NAME="RA34504ST-45">45 </A>
Yamago, S.;. Miyazoe, H.; Iida, K.; Yoshida, J. unpublished results.
<A NAME="RA34504ST-46">46 </A>
Chatgilialoglu C.
Ingold KU.
Scaiano JC.
J. Am. Chem. Soc.
1982,
104:
5123
<A NAME="RA34504ST-47">47 </A>
Fukuzumi S.
Bull. Chem. Soc. Jpn.
1997,
70:
1
<A NAME="RA34504ST-48A">48a </A>
Yamago S.
Iida K.
Yoshida J.
J. Am. Chem. Soc.
2002,
124:
2874
<A NAME="RA34504ST-48B">48b </A>
Yamago S.
Iida K.
Yoshida J.
J. Am. Chem. Soc.
2002,
124:
13666
<A NAME="RA34504ST-49A">49a </A>
Handbook of Radical Polymerization
Matyjaszewski K.
Davis TP.
Wiley-Interscience;
New York:
2002.
<A NAME="RA34504ST-49B">49b </A>
Matyjaszewski K.
Controlled/Living Radical Polymerization. Progress in ATRP, NMP, and RAFT
American Chemical Society;
Washington DC:
2000.
<A NAME="RA34504ST-49C">49c </A>
Hawker CJ.
Bosman AW.
Harth E.
Chem. Rev.
2001,
101:
3661
<A NAME="RA34504ST-49D">49d </A>
Matyjaszewski K.
Xia J.
Chem. Rev.
2001,
101:
2921
<A NAME="RA34504ST-49E">49e </A>
Kamigaito M.
Ando T.
Sawamoto M.
Chem. Rev.
2001,
101:
3689
<A NAME="RA34504ST-50">50 </A>
Oka M.
Tatemoto M. In
Contemporary Topics in Polymer Science
Bailey WJ.
Tsuruta T.
Plenum;
New York:
1984.
p.763-777
<A NAME="RA34504ST-51A">51a </A>
Matyjaszewski K.
Gaynor S.
Wang J.-S.
Macromolecules
1995,
28:
2093
<A NAME="RA34504ST-51B">51b </A>
Iovu MC.
Matyjaszewski K.
Macromolecules
2003,
36:
9346
<A NAME="RA34504ST-52">52 </A>
Kwon TS.
Kumazawa S.
Yokoi T.
Kondo S.
Kunisada H.
Yuki Y.
J. Macromol. Sci., Pure Appl. Chem.
1997,
A34:
1553
<A NAME="RA34504ST-53">53 </A>
Takagi K.
Soyano A.
Kwon TS.
Kunisada H.
Yuki Y.
Polym. Bull.
1999,
43:
143
<A NAME="RA34504ST-54">54 </A>
Yamago S.
Iida K.
Nakajima M.
Yoshida J.
Macromolecules
2003,
36:
3793
<A NAME="RA34504ST-55">55 </A>
Goto A.
Ohno K.
Fukuda T.
Macromolecules
1998,
31:
2809