RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2011(4): 517-538
DOI: 10.1055/s-0030-1258328
DOI: 10.1055/s-0030-1258328
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents
Weitere Informationen
Received
19 September 2010
Publikationsdatum:
15. November 2010 (online)
Publikationsverlauf
Publikationsdatum:
15. November 2010 (online)
Abstract
α-Functionalized carbonyl compounds are versatile intermediates in organic synthesis. A broad range of both carbon and heteroatom substituents can be introduced into the α-position of carbonyl compounds using hypervalent iodine reagents. Herein we summarize the use of these environmentally benign reagents with particular emphasis on catalytic and asymmetric methodology developed over the past decade.
1 Introduction
2 Oxygenation
3 Halogenation
4 Trifluoromethylation
5 Arylation
6 Alkynylation and Alkenylation
7 Homocoupling
8 Functionalization of α,β-Unsaturated Carbonyl Compounds
9 Miscellaneous
10 Summary
Key words
catalysis - asymmetric synthesis - oxidation - hypervalent iodine - C-C bond formation
- 1
Bertelsen S.Jorgensen KA. Chem. Soc. Rev. 2009, 38: 2178 - 2
Johansson CC.Colacot TJ. Angew. Chem. Int. Ed. 2010, 49: 676 -
3a
Wirth T. Angew. Chem. Int. Ed. 2005, 44: 3656 -
3b
Richardson RD.Wirth T. Angew. Chem. Int. Ed. 2006, 45: 4402 -
4a
Zhdankin VV.Stang PJ. Chem. Rev. 2008, 108: 5299 -
4b
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
4c
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
4d
Varvoglis A. Tetrahedron 1997, 53: 1179 -
5a
Wirth T. In Topics in Current Chemistry Vol. 224: Springer; Berlin: 2003. -
5b
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; New York: 1997. -
5c
Varvoglis A. The Organic Chemistry of Polycoordinated Iodine Wiley-VCH; Weinheim: 1992. - 6
Wirth T. Angew. Chem. Int. Ed. 2001, 40: 2812 - 7
Merritt EA.Olofsson B. Angew. Chem. Int. Ed. 2009, 48: 9052 - 8
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
9a
Ochiai M.Takeuchi Y.Katayama T.Sueda T.Miyamoto K. J. Am. Chem. Soc. 2005, 127: 12244 -
9b
Dohi T.Maruyama A.Yoshimura M.Morimoto K.Tohma H.Kita Y. Angew. Chem. Int. Ed. 2005, 44: 6193 -
9c
Dohi T.Kita Y. Chem. Commun. 2009, 2073 -
9d
Ochiai M.Miyamoto K. Eur. J. Org. Chem. 2008, 4229 -
10a
Quideau S.Lyvinec G.Marguerit M.Bathany K.Ozanne-Beaudenon A.Buffeteau T.Cavagnat D.Chénedé A. Angew. Chem. Int. Ed. 2009, 48: 4605 -
10b
Uyanik M.Yasui T.Ishihara K. Angew. Chem. Int. Ed. 2010, 49: 2175 -
10c
Uyanik M.Okamoto H.Yasui T.Ishihara K. Science 2010, 328: 1376 -
10d
Dohi T.Maruyama A.Takenaga N.Senami K.Minamitsuji Y.Fujioka H.Caemmerer SB.Kita Y. Angew. Chem. Int. Ed. 2008, 47: 3787 -
11a
Prakash O.Saini N.Tanwar MP.Moriarty RM. Contemp. Org. Synth. 1995, 2: 121 -
11b
Moriarty RM.Prakash O. Org. React. 1999, 273 - 12
Pouysegu L.Deffieux D.Quideau S. Tetrahedron 2010, 66: 2235 - 13
Merino P.Tejero T. Angew. Chem. Int. Ed. 2004, 43: 2995 - 14
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138 - 15
Neilands O.Karele B. Zh. Org. Khim. 1970, 6: 885 - 16
Kumar R. Synlett 2007, 2764 - 17
Koser GF.Relenyi AG.Kalos AN.Rebrovic L.Wettach RH. J. Org. Chem. 1982, 47: 2487 - 18
Lodaya JS.Koser GF. J. Org. Chem. 1988, 53: 210 - 19
Hatzigrigoriou E.Varvoglis A.Bakola-Christianopoulou M. J. Org. Chem. 1990, 55: 315 - 20
Kumar D.Sundaree MS.Patel G.Rao VS.Varma RS. Tetrahedron Lett. 2006, 47: 8239 - 21
Tuncay A.Dustman JA.Fisher G.Tuncay CI.Suslick KS. Tetrahedron Lett. 1992, 33: 7647 - 22
Nabana T.Togo H. J. Org. Chem. 2002, 67: 4362 - 23
Lee JC.Kim S.Ku CH.Choi HJ.Lee YC. Bull. Korean Chem. Soc. 2002, 23: 1503 - 24
Lee JC.Yoo ES.Park JY. Bull. Korean Chem. Soc. 2004, 25: 1457 - 25
Xie Y.-Y.Chen Z.-C. Synth. Commun. 2002, 32: 1875 - 26
Karade NN.Tiwari GB.Gampawar SV.Shinde SV. Heteroat. Chem. 2009, 20: 172 - 27
Tanaka A.Togo H. Synlett 2009, 3360 - 28
Yusubov MS.Wirth T. Org. Lett. 2005, 7: 519 - 29
Lee JC.Choi J.-H. Synlett 2001, 234 - 30
Yu J.Tian J.Zhang C. Adv. Synth. Catal. 2010, 352: 531 - 31
Ueno M.Nabana T.Togo H. J. Org. Chem. 2003, 68: 6424 - 32
Shah A.-u.-HA.Khan ZA.Choudhary N.Loholter C.Schafer S.Marie GPL.Farooq U.Witulski B.Wirth T. Org. Lett. 2009, 11: 3578 - 33
Richardson RD.Zayed JM.Altermann S.Smith D.Wirth T. Angew. Chem. Int. Ed. 2007, 46: 6529 - 34
Karade NN.Tiwari GB.Shinde SV.Gampawar SV.Kondre JM. Tetrahedron Lett. 2008, 49: 3441 - 35
Mahajan US.Akamanchi KG. Synlett 2008, 987 - 36
Abe S.Sakuratani K.Togo H. Synlett 2001, 22 - 37
Abe S.Sakuratani K.Togo H. J. Org. Chem. 2001, 66: 6174 - 38
Nicolaou KC.Montagnon T.Ulven T.Baran PS.Zhong YL.Sarabia F. J. Am. Chem. Soc. 2002, 124: 5718 - 39
Tohma H.Maruyama A.Maeda A.Maegawa T.Dohi T.Shiro M.Morita T.Kita Y. Angew. Chem. Int. Ed. 2004, 43: 3595 - 40
Dohi T.Maruyama A.Yoshimura M.Morimoto K.Tohma H.Shiro M.Kita Y. Chem. Commun. 2005, 2205 - 41
Moroda A.Togo H. Tetrahedron 2006, 62: 12408 - 42
Handy ST.Okello M. J. Org. Chem. 2005, 70: 2874 - 43
Yamamoto Y.Togo H. Synlett 2006, 798 - 44
Yamamoto Y.Kawano Y.Toy PH.Togo H. Tetrahedron 2007, 63: 4680 - 45
Akiike J.Yamamoto Y.Togo H. Synlett 2007, 2168 - 46
Wirth T.Hirt UH. Tetrahedron: Asymmetry 1997, 8: 23 - 47
Hirt UH.Spingler B.Wirth T. J. Org. Chem. 1998, 63: 7674 - 48
Hirt UH.Schuster MFH.French AN.Wiest OG.Wirth T. Eur. J. Org. Chem. 2001, 1569 - 49
Richardson RD.Page TK.Altermann S.Paradine SM.French AN.Wirth T. Synlett 2007, 538 - 50
Altermann SM.Richardson RD.Page TK.Schmidt RK.Holland E.Mohammed U.Paradine SM.French AN.Richter C.Bahar AM.Witulski B.Wirth T. Eur. J. Org. Chem. 2008, 5315 - 51
Farooq U.Schäfer S.Shah A.-u.-HA.Freudendahl DM.Wirth T. Synthesis 2010, 1023 - 52
Moriarty RM.Hu H.Gupta SC. Tetrahedron Lett. 1981, 22: 1283 - 53
Moriarty RM.Hu H. Tetrahedron Lett. 1981, 22: 2747 - 54
Moriarty RM.Hou K.-C.Prakash I.Arora SK. Org. Synth. 1986, 64: 138 - 55
Moriarty RM.Berglund BA.Penmasta R. Tetrahedron Lett. 1992, 33: 6065 - 56
Moriarty RM. J. Org. Chem. 2005, 70: 2893 - 57
Togo H.Abe S.Nogami G.Yokoyama M. Bull. Chem. Soc. Jpn. 1999, 72: 2351 - 58
Ley SV.Thomas AW.Finch H. J. Chem. Soc., Perkin Trans. 1 1999, 669 - 59
Kirsch SF. J. Org. Chem. 2005, 70: 10210 - 60
Duschek A.Kirsch SF. Chem. Eur. J. 2009, 15: 10713 - 61
Chen C.Feng X.Zhang G.Zhao Q.Huang G. Synthesis 2008, 3205 - 62
Engqvist M.Casas J.Sunden H.Ibrahem I.Cordova A. Tetrahedron Lett. 2005, 46: 2053 - 63
Mizukami F.Ando M.Tanaka T.Imamura J. Bull. Chem. Soc. Jpn. 1978, 51: 335 - 64
Podolešov B. J. Org. Chem. 1984, 49: 2644 - 65
Sheng J.Li X.Tang M.Gao B.Huang G. Synthesis 2007, 1165 - 66
Kumar S.Kumar A.Gupta RK.Kumar D. Synth. Commun. 2008, 38: 338 - 67
Koser GF.Lodaya JS.Ray DG.Kokil PB. J. Am. Chem. Soc. 1988, 110: 2987 - 68
Moriarty RM.Condeiu C.Tao A.Prakash O. Tetrahedron Lett. 1997, 38: 2401 - 69
Pan Z.-L.Liu X.-Y.Liang Y.-M. Tetrahedron Lett. 2004, 45: 4101 - 70
Moriarty RM.Vaid RK.Ravikumar VT.Vaid BK.Hopkins TE. Tetrahedron 1988, 44: 1603 - 71
Prakash O.Saini N.Sharma PK. Synlett 1994, 221 - 72
Rodriguez S.Wipf P. Synthesis 2004, 2767 - 73
Prakash O.Goyal S. Synthesis 1992, 629 - 74
Karade NN.Gampawar SV.Kondre JM.Shinde SV. Tetrahedron Lett. 2008, 49: 4402 - 75
Murphy GK.West FG. Org. Lett. 2006, 8: 4359 - 76
Moriarty RM.Vaid RK.Hopkins TE.Vaid BK.Prakash O. Tetrahedron Lett. 1990, 31: 201 - 77
Uyanik M.Yasui T.Ishihara K. Bioorg. Med. Chem. Lett. 2009, 19: 3848 - 78
Ye Y.Wang L.Fan R. J. Org. Chem. 2010, 75: 1760 - 79
Hara S.Sekiguchi M.Ohmori A.Fukuhara T.Yoneda N. Chem. Commun. 1996, 1899 - 80
Hara S.Hatakeyama T.Chen S.-Q.Ishi-i K.Yoshida M.Sawaguchi M.Fukuhara T.Yoneda N. J. Fluorine Chem. 1998, 87: 189 - 81
Yoshida M.Fujikawa K.Sato S.Hara S. ARKIVOC 2003, (vi): 36 - 82
Sato S.Yoshida M.Hara S. Synthesis 2005, 2602 -
83a
Greaney MF.Motherwell WB. Tetrahedron Lett. 2000, 41: 4463 -
83b
Motherwell WB.Greaney MF.Tocher DA. J. Chem. Soc., Perkin Trans. 1 2002, 2809 -
84a
Greaney MF.Motherwell WB. Tetrahedron Lett. 2000, 41: 4467 -
84b
Motherwell WB.Greaney MF.Edmunds JJ.Steed JW. J. Chem. Soc., Perkin Trans. 1 2002, 2816 - 85
Arrica MA.Wirth T. Eur. J. Org. Chem. 2005, 2005: 395 -
86a
Dneprovskii AS.Krainyuchenko IU.Temnikova TI. Zh. Org. Khim. 1978, 14: 1514 -
86b
Moskovkina TV.Vysotskii VI. Zh. Org. Khim. 1991, 27: 833 - 87
Zbiral E.Rasberger M. Tetrahedron 1969, 25: 1871 - 88
Ibrahim H.Kleinbeck F.Togni A. Helv. Chim. Acta 2004, 87: 605 - 89
Podgorsek A.Jurisch M.Stavber S.Zupan M.Iskra J.Gladysz JA. J. Org. Chem. 2009, 74: 3133 - 90
Akula R.Galligan M.Ibrahim H. Chem. Commun. 2009, 6991 - 91
Lee JC.Jin YS. Synth. Commun. 1999, 29: 2769 - 92
Lee JC.Park JY.Yoon SY.Bae YH.Lee SJ. Tetrahedron Lett. 2004, 45: 191 - 93
Shimizu M.Hiyama T. Angew. Chem. Int. Ed. 2005, 44: 214 -
94a
Eisenberger P.Gischig S.Togni A. Chem. Eur. J. 2006, 12: 2579 -
94b
Niedermann K.Welch JM.Koller R.Cvengros J.Santschi N.Battaglia P.Togni A. Tetrahedron 2010, 66: 5753 -
95a
Kieltsch I.Eisenberger P.Togni A. Angew. Chem. Int. Ed. 2007, 46: 754 -
95b
Kieltsch I.Eisenberger P.Stanek K.Togni A. Chimia 2008, 62: 260 - 96
Allen AE.MacMillan DWC. J. Am. Chem. Soc. 2010, 132: 4986 - 97
Umemoto T. Chem. Rev. 1996, 96: 1757 - 98
Burtoloso ACB. Synlett 2009, 320 - 99
Bellina F.Rossi R. Chem. Rev. 2009, 110: 1082 - 100
Beringer FM.Forgione PS.Yudis MD. Tetrahedron 1960, 8: 49 - 101
Beringer FM.Galton SA.Huang SJ. J. Am. Chem. Soc. 1962, 84: 2819 - 102
Beringer FM.Forgione PS. Tetrahedron 1963, 19: 739 - 103
Beringer FM.Forgione PS. J. Org. Chem. 1963, 28: 714 - 104
Beringer FM.Daniel WJ.Galton SA.Rubin G. J. Org. Chem. 1966, 31: 4315 - 105
Chen Z.Jin Y.Stang PJ. J. Org. Chem. 1987, 52: 4115 - 106
Hampton KG.Harris TM.Hauser CR. J. Org. Chem. 1964, 29: 3511 - 107
Hampton KG.Harris TM.Hauser CR. Org. Synth. 1971, 51: 128 - 108
Ryan JH.Stang PJ. Tetrahedron Lett. 1997, 38: 5061 - 109
Gao P.Portoghese PS. J. Org. Chem. 1995, 60: 2276 - 110
Gao P.Larson DL.Portoghese PS. J. Med. Chem. 1998, 41: 3091 - 111
Oh CH.Kim JS.Jung HH. J. Org. Chem. 1999, 64: 1338 - 112
Chen K.Koser GF. J. Org. Chem. 1991, 56: 5764 - 113
Iwama T.Birman VB.Kozmin SA.Rawal VH. Org. Lett. 1999, 1: 673 - 114
Kozmin SA.Rawal VH. J. Am. Chem. Soc. 1998, 120: 13523 - 115
Ochiai M.Kitagawa Y.Takayama N.Takaoka Y.Shiro M. J. Am. Chem. Soc. 1999, 121: 9233 - 116
Aggarwal VK.Olofsson B. Angew. Chem. Int. Ed. 2005, 44: 5516 - 117
Norrby P.-O.Petersen TB.Bielawski M.Olofsson B. Chem. Eur. J. 2010, 16: 8251 - 118
Bella M.Kobbelgaard S.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 3670 - 119
Beringer FM.Galton SA. J. Org. Chem. 1963, 28: 3417 - 120
Ochiai M.Kitagawa Y.Toyonari M. ARKIVOC 2003, (vi): 43 - 121
Kita Y.Tohma H.Hatanaka K.Takada T.Fujita S.Mitoh S.Sakurai H.Oka S. J. Am. Chem. Soc. 1994, 116: 3684 - 122
Arisawa M.Ramesh NG.Nakajima M.Tohma H.Kita Y. J. Org. Chem. 2001, 66: 59 -
123a
Tamura Y.Yakura T.Shirouchi Y.Haruta J.-I. Chem. Pharm. Bull. 1986, 34: 1061 -
123b
Wang H.-M.Lin M.-C.Chen L.-C. Heterocycles 1994, 38: 1519 - 124
Tang S.Peng P.Pi S.-F.Liang Y.Wang N.-X.Li J.-H. Org. Lett. 2008, 10: 1179 - 125
Stang PJ. In Modern Acetylene ChemistryStang PJ. VCH; Weinheim: 1995. - 126
Ochiai M. J. Organomet. Chem. 2000, 611: 494 - 127
Beringer FM.Galton SA. J. Org. Chem. 1965, 30: 1930 - 128
Ochiai M.Kunishima M.Nagao Y.Fuji K.Shiro M.Fujita E. J. Am. Chem. Soc. 1986, 108: 8281 - 129
Kitamura T.Nagata K.Taniguchi H. Tetrahedron Lett. 1995, 36: 1081 - 130
Ochiai M.Ito T.Takaoka Y.Masaki Y.Kunishima M.Tani S.Nagao Y. J. Chem. Soc., Chem. Commun. 1990, 118 - 131
Bachi MD.Bar-Ner N.Crittell CM.Stang PJ.Williamson BL. J. Org. Chem. 1991, 56: 3912 - 132
Bachi MD.Bar-Ner N.Stang PJ.Williamson BL. J. Org. Chem. 1993, 58: 7923 - 133
Ochiai M.Kitagawa Y.Toyonari M.Uemura K.Oshima K.Shiro M. J. Org. Chem. 1997, 62: 8001 - 134
Fernández González D.Brand J.Waser J. Chem. Eur. J. 2010, 16: 9457 - 135
Moriarty RM.Vaid RK. Synthesis 1990, 431 -
136a
Moriarty RM.Prakash O.Duncan MP. J. Chem. Soc., Chem. Commun. 1985, 420 -
136b
Moriarty RM.Prakash O.Duncan MP. J. Chem. Soc., Perkin Trans. 1 1987, 559 - 137
Zhdankin VV.Tykwinski R.Berglund B.Mullikin M.Caple R.Zefirov NS.Koz’min AS. J. Org. Chem. 1989, 54: 2609 - 138
Zhdankin VV.Mullikin M.Tykwinski R.Berglund B.Caple R.Zefirov NS.Koz’min AS. J. Org. Chem. 1989, 54: 2605 - 139
Yan J.Zhong L.Chen Z. J. Org. Chem. 1991, 56: 459 -
140a
Kim JW.Lee J.-J.Lee S.-H.Ahn K.-H. Synth. Commun. 1998, 28: 1287 -
140b
Kise N.Ueda T.Kumada K.Terao Y.Ueda N. J. Org. Chem. 2000, 65: 464 - 141
Karade NN.Shirodkar SG.Patil MN.Potrekar RA.Karade HN. Tetrahedron Lett. 2003, 44: 6729 - 142
Ochiai M.Nakanishi A.Suefuji T. Org. Lett. 2000, 2: 2923 - 143
McQuaid KM.Pettus TRR. Synlett 2004, 2403 - 144
Pettus LH.Van De Water RW.Pettus TRR. Org. Lett. 2001, 3: 905 - 145
Moorthy JN.Senapati K.Kumar S. J. Org. Chem. 2009, 74: 6287 - 146
Lee S.MacMillan DWC. Tetrahedron 2006, 62: 11413 - 147
Evans DA.Faul MM.Bilodeau MT. J. Org. Chem. 1991, 56: 6744 - 148
Evans DA.Bilodeau MT.Faul MM. J. Am. Chem. Soc. 1994, 116: 2742 - 149
Evans DA.Faul MM.Bilodeau MT.Anderson BA.Barnes DM. J. Am. Chem. Soc. 1993, 115: 5328 -
150a
Li Z.Quan RW.Jacobsen EN. J. Am. Chem. Soc. 1995, 117: 5889 -
150b
Quan RW.Li Z.Jacobsen EN. J. Am. Chem. Soc. 1996, 118: 8156 - 151
Gillespie KM.Sanders CJ.O’Shaughnessy P.Westmoreland I.Thickitt CP.Scott P. J. Org. Chem. 2002, 67: 3450 - 152
Wang X.Ding K. Chem. Eur. J. 2006, 12: 4568 - 153
Krasnova LB.Hili RM.Chernoloz OV.Yudin AK. ARKIVOC 2005, (iv): 26 - 154
Xu J.Ma L.Jiao P. Chem. Commun. 2004, 1616 - 155
Ma L.Du D.-M.Xu J. J. Org. Chem. 2005, 70: 10155 - 156
Wang G.-W.Wu X.-L. Adv. Synth. Catal. 2007, 349: 1977 - 157
Wu X.-L.Wang G.-W. J. Org. Chem. 2007, 72: 9398 - 158
Wu X.-L.Xia J.-J.Wang G.-W. Org. Biomol. Chem. 2008, 6: 548 - 159
Wu X.-L.Wang G.-W. Tetrahedron 2009, 65: 8802 - 160
Rebrovic L.Koser GF. J. Org. Chem. 1984, 49: 2462 - 161
Prakash O.Kumar R.Sharma D.Pannu K.Kamal R. Synlett 2007, 2189 - 162
Moriarty RM.Khosrowshahi JS.Prakash O. Tetrahedron Lett. 1985, 26: 2961 -
163a
Miki Y.Fujita R.Matsushita K.-i. J. Chem. Soc., Perkin Trans. 1 1998, 2533 -
163b
Miki Y.Kobayashi S.Ogawa N.Hachiken H. Synlett 1994, 1001 - 164
Kawamura Y.Maruyama M.Tokuoka T.Tsukayama M. Synthesis 2002, 2490 -
165a
Hossain MM.Tokuoka T.Yamashita K.Kawamura Y.Tsukayama M. Synth. Commun. 2006, 36: 1201 -
165b
Hossain MM.Kawamura Y.Yamashita K.Tsukayama M. Tetrahedron 2006, 62: 8625 - 166
Singh OV.Garg CP.Kapoor RP. Synthesis 1990, 1025 - 167
Ngatimin M.Gartshore CJ.Kindler JP.Naidu S.Lupton DW. Tetrahedron Lett. 2009, 50: 6008 - 168
Robins MJ.Barr PJ.Giziewicz J. Can. J. Chem. 1982, 60: 554 -
169a
Comins DL.Joseph SP.Chen X. Tetrahedron Lett. 1995, 36: 9141 -
169b
Comins DL.Kuethe JT.Miller TM.Février FC.Brooks CA. J. Org. Chem. 2005, 70: 5221 -
170a
Kita Y.Yakura T.Tohma H.Kikuchi K.Tamura Y. Tetrahedron Lett. 1989, 30: 1119 -
170b
Kita Y.Tohma H.Inagaki M.Hatanaka K.Yakura T. J. Am. Chem. Soc. 1992, 114: 2175 - 171
Adam W.Gogonas EP.Nyxas IA.Hadjiarapoglou LP. Synthesis 2007, 3211 - 172
Lee JC.Kim S.Shin WC. Synth. Commun. 2000, 30: 4271 - 173
Xie Y.-Y.Chen Z.-C. Synth. Commun. 2001, 31: 3145 - 174
Prakash O.Kaur H.Batra H.Rani N.Singh SP.Moriarty RM. J. Org. Chem. 2001, 66: 2019 - 175
Prakash O.Kaur H.Pundeer R.Dhillon RS.Singh SP. Synth. Commun. 2003, 33: 4037