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Synthesis 2003(5): 0633-0655
DOI: 10.1055/s-2003-38064
DOI: 10.1055/s-2003-38064
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York
Indium in Organic Synthesis
Further Information
Received
20 January 2003
Publication Date:
21 March 2003 (online)
Publication History
Publication Date:
21 March 2003 (online)
Abstract
The various applications of indium in organic synthesis are highlighted in this review. Major fields are Barbier-type reactions, especially allyl additions to carbonyl compounds, and Reformatsky reactions. Special emphasis is placed on reactions, which have been examined only recently, i.e. reductions of various functionalities, indium-catalyzed reactions and palladium/indium-mediated reactions.
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1 Introduction
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2 Barbier-Type Reactions
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2.1 Indium-Mediated Additions to Aldehydes and Ketones
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2.2 The Role of the Allyl Halide
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2.3 Diastereoselectivity
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2.4 Regioselectivity
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2.5 Enantioselectivity
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2.6 Indium-Mediated Additions to Further Carbonyl Derivatives
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2.7 Indium-Mediated Additions to C-C Multiple Bonds
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2.8 Reaction of Non-Allylic Substrates in Barbier-Type Reactions
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3 Palladium-Catalyzed Allylic Substitutions and Cross-Couplings of Indium Intermediates
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4 Reformatsky-Type Reactions
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5 Indium-Catalyzed Reactions
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6 Nucleophilic Substitutions Using Intermediate Allylindium Compounds
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7 Allylindium Reagents
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8 Indium-Mediated Reductions
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8.1 Reduction and Deoxygenation of N-Containing Functionalities
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8.2 Reductive Dehalogenations
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8.3 Reduction of Carbonyl Groups
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8.4 Miscellaneous Reductions
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9 Conclusion
Key Words
indium - allyl addition - Barbier reaction - Reformatsky reaction - reductions
- 1
Cintas P. Synlett 1995, 1087 - 2
Araki S.Ito H.Butsugan Y. J. Org. Chem. 1988, 53: 1831 - 3
Chan TH.Li C.-J.Lee MC.Wei ZY. Can. J. Chem. 1994, 72: 1181 - 4
Li C.-J. Tetrahedron 1996, 52: 5643 - 5
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media Wiley-Interscience; New York: 1997. - 6
Marshall JA. Chemtracts Org. Chem. 1997, 10: 481 - 7
Hashmi ASK. J. Prakt. Chem. 1998, 340: 84 - 8
Paquette LA. In Green Chemistry. Frontiers in Benign Chemical Syntheses and ProcessesAnastas PT.Williamson TC. Oxford University Press; Oxford: 1998. p.250 - 9
Lubineau A.Augé J.Queneau Y. In Organic Synthesis in WaterGrieco PA. Blackie Academic; London: 1998. p.102 - 10
Lainé D. Synlett 1999, 1331 - 11
Chauhan KK.Frost CG. J. Chem. Soc., Perkin Trans. 1 2000, 3015 - 12
Ranu BC. Eur. J. Org. Chem. 2000, 2347 - 13
Li CJ.Chan TH. Tetrahedron Lett. 1991, 32: 7017 - 14
Standard
Potentials in Aqueous Solution
Bard AJ.Parsons R.Jordan J. Marcel Dekker; New York: 1985. - 15
Weidlein J. In Gmelin Handbook of Inorganic and Organometallic Chemistry In Organoindium Compounds 1Petz W. Springer; Berlin: 1991. 8th Ed. - 16
Barbier P. C. R. Hebd. Seances Acad. Sci. 1898, 128: 110 - 17
Crestia D.Guérard C.Veschambre H.Hecquet L.Demuynck C.Bolte J. Tetrahedron: Asymmetry 2001, 12: 869 - 18
Reetz MT.Haning H. J. Organomet. Chem. 1997, 541: 117 - 19
Loh T.-P.Ho DS.-C.Chua G.-L.Sim K.-Y. Synlett 1997, 563 - 20
Carda M.Castillo E.Rodríguez S.Murga J.Marco JA. Tetrahedron: Asymmetry 1998, 9: 1117 - 21
Loh T.-P.Huang J.-M.Xu K.-C.Goh S.-H.Vittal JJ. Tetrahedron Lett. 2000, 41: 6511 - 22
Nair V.Jayan CN. Tetrahedron Lett. 2000, 41: 1091 - 23
Kang S.-K.Baik T.-G.Jiao X.-H. Synth. Commun. 2002, 32: 75 - 24
Li C.-J.Lu Y.-Q. Tetrahedron Lett. 1995, 36: 2721 - 25
Lee PH.Lee K.Chang S. Synth. Commun. 2001, 31: 3189 - 26
Yi X.-H.Haberman JX.Li C.-J. Synth. Commun. 1998, 28: 2999 - 27
Isaac MB.Chan T.-H. Tetrahedron Lett. 1995, 36: 8957 - 28
Diana S.-CH.Sim K.-Y.Loh T.-P. Synlett 1996, 263 - 29
Kumar S.Kaur P.Chimni SS. Synlett 2002, 573 - 30
Cha JH.Pae AN.Choi KII.Cho YS.Koh HY.Lee E. J. Chem. Soc., Perkin Trans. 1 2001, 2079 - 31
Paquette LA.Bennett GD.Isaac MB.Chhatriwalla A. J. Org. Chem. 1998, 63: 1836 - 32
Isaac MB.Paquette LA. J. Org. Chem. 1997, 62: 5333 - 33
Loh T.-P.Hu Q.-Y.Vittal JJ. Synlett 2000, 523 - 34
Méndez-Andino J.Paquette LA. Adv. Synth. Catal. 2002, 344: 303 - 35
Paquette LA.Mitzel TM. J. Org. Chem. 1996, 61: 8799 - 36
Maguire RJ.Mulzer J.Bats JW. J. Org. Chem. 1996, 61: 6936 - 37
Khan FA.Prabhudas B. Tetrahedron 2000, 56: 7595 - 38
Loh T.-P.Li X.-R. Tetrahedron Lett. 1997, 38: 869 - 39
Li C.-J. Tetrahedron Lett. 1995, 36: 517 - 40
Choudhury PK.Foubelo F.Yus M. Tetrahedron Lett. 1998, 39: 3581 - 41
Kirihara M.Takuwa T.Takizawa S.Momose T. Tetrahedron Lett. 1997, 38: 2853 - 42
Araki S.Hirashita T.Shimizu H.Yamamura H.Kawai M.Butsugan Y. Tetrahedron Lett. 1996, 37: 8417 - 43
Bardot V.Remuson R.Gelas-Mialhe Y.Gramain J.-C. Synlett 1996, 37 - 44
Canac Y.Levoirier E.Lubineau A. J. Org. Chem. 2001, 66: 3206 - 45
Lubineau A.Canac Y.Le Goff N. Adv. Synth. Catal. 2002, 344: 319 - 46
Li C.-J.Chen D.-L.Lu Y.-Q.Haberman JX.Mague JT. J. Am. Chem. Soc. 1996, 118: 4216 - 47
Bryan VJ.Chan T.-H. Tetrahedron Lett. 1996, 37: 5341 - 48
Cavallaro CL.Herpin T.McGuinness BF.Shimshock YC.Dolle RE. Tetrahedron Lett. 1999, 40: 2711 - 49
Paquette LA.Mitzel TM. Tetrahedron Lett. 1995, 36: 6863 - 50
Paquette LA.Mitzel TM. J. Am. Chem. Soc. 1996, 118: 1931 - 51
Paquette LA.Mitzel TM.Isaac MB.Crasto CF.Schomer WW. J. Org. Chem. 1997, 62: 4293 - 52
Paquette LA.Lobben PC. J. Am. Chem. Soc. 1996, 118: 1917 - 53
Kempf DJ. J. Org. Chem. 1986, 51: 3921 - 54
Chan T.-H.Li C.-J. J. Chem. Soc., Chem. Commun. 1992, 747 - 55
Chan T.-H.Lee M.-C. J. Org. Chem. 1995, 60: 4228 - 56
Warwel M.Fessner W.-D. Synlett 2000, 865 - 57
Kim E.Gordon DM.Schmid W.Whitesides GM. J. Org. Chem. 1993, 58: 5500 - 58
Gordon DM.Whitesides GM. J. Org. Chem. 1993, 58: 7937 - 59
Choi S.-K.Lee S.Whitesides GM. J. Org. Chem. 1996, 61: 8739 - 60
Gao J.Härter R.Gordon DM.Whitesides GM. J. Org. Chem. 1994, 59: 3714 - 61
Prenner RH.Binder WH.Schmid W. Liebigs Ann. Chem. 1994, 73 - 62
Wang R.Lim C.-M.Tan C.-H.Lim B.-K.Sim K.-Y.Loh T.-P. Tetrahedron: Asymmetry 1995, 6: 1825 - 63
Steurer S.Podlech J. Eur. J. Org. Chem. 1999, 1551 - 64
Steurer S.Podlech J. Adv. Synth. Catal. 2001, 343: 251 - 65
Steurer S.Podlech J. Synthesis 2002, 945 - 66
Chappell MD.Halcomb RL. Org. Lett. 2000, 2: 2003 - 67
Steurer S.Podlech J. Eur. J. Org. Chem. 2002, 899 - 69
Paquette LA.Stephanian M.Mallavadhani UV.Cutarelli TD.Lowinger TB.Klemeyer HJ. J. Org. Chem. 1996, 61: 7492 - 70
Lee PH.Ahn H.Lee K.Sung S.-y.Kim S. Tetrahedron Lett. 2001, 42: 37 - 71
Jang DO.Cho DH. Synlett 2002, 631 - 72
Loh T.-P.Zhou J.-R.Yin Z. Org. Lett. 1999, 1: 1855 - 73
Loh T.-P.Zhou J.-R.Li X.-R. Tetrahedron Lett. 1999, 40: 9333 - 74
Lee JG.Choi KI.Pae AN.Koh HY.Kang Y.Cho YS. J. Chem. Soc., Perkin Trans. 1 2002, 1314 - 75
Beuchet P.Le Marrec N.Mosset P. Tetrahedron Lett. 1992, 33: 5959 - 76
Choudhury PK.Foubelo F.Yus M. J. Org. Chem. 1999, 64: 3376 - 77
Loh T.-P.Ho DS.-C.Xu K.-C.Sim K.-Y. Tetrahedron Lett. 1997, 38: 865 - 78
Cerè V.Peri F.Pollicino S.Ricci A. Synlett 1999, 1585 - 79
Miyabe H.Nishimura A.Ueda M.Naito T. Chem. Commun. 2002, 1454 - 80
Chan TH.Lu W. Tetrahedron Lett. 1998, 39: 8605 - 81
Lu W.Chan TH. J. Org. Chem. 2000, 65: 8589 - 82
Lu W.Chan TH. J. Org. Chem. 2001, 66: 3467 - 83
Yadav JS.Srinivas D.Reddy GS.Bindu KH. Tetrahedron Lett. 1997, 38: 8745 - 84
Bryan VJ.Chan T.-H. Tetrahedron Lett. 1997, 38: 6493 - 85
Yoo BW.Choi KH.Lee SJ.Nam GS.Chang KY.Kim SH.Kim JH. Synth. Commun. 2002, 32: 839 - 86
Sabitha G.Reddy CS.Babu RS.Yadav JS. Synlett 2001, 1787 - 87
Araki S.Katsumura N.Ito H.Butsugan Y. Tetrahedron Lett. 1989, 30: 1581 - 88
Araki S.Shimizu T.Johar PS.Jin S.-J.Butsugan Y. J. Org. Chem. 1991, 56: 2538 - 89
Fujiwara N.Yamamoto Y. Tetrahedron Lett. 1998, 39: 4729 - 90
Wang L.Sun X.Zhang Y. Synth. Commun. 1998, 28: 3263 - 91
Araki S.Horie T.Kato M.Hirashita T.Yamamura H.Kawai M. Tetrahedron Lett. 1999, 40: 2331 - 92
Araki S.Kamei T.Igarashi Y.Hirashita T.Yamamura H.Kawai M. Tetrahedron Lett. 1999, 40: 7999 - 93
Araki S.Nakano H.Subburaj K.Hirashita T.Shibutani K.Yamamura H.Kawai M.Butsugan Y. Tetrahedron Lett. 1998, 39: 6327 - 94
Araki S.Shiraki F.Tanaka T.Nakano H.Subburaj K.Hirashita T.Yamamura H.Kawai M. Chem.-Eur. J. 2001, 7: 2784 - 95
Araki S.Kenji O.Shiraki F.Hirashita T. Tetrahedron Lett. 2002, 43: 8033 - 96
Araki S.Usui H.Kato M.Butsugan Y. J. Am. Chem. Soc. 1996, 118: 4699 - 97
Araki S.Imai A.Shimizu K.Yamada M.Mori A.Butsugan Y. J. Org. Chem. 1995, 60: 1841 - 98
Fujiwara N.Yamamoto Y. J. Org. Chem. 1997, 62: 2318 - 99
Ranu BC.Majee A. Chem. Commun. 1997, 1225 - 100
Augé J.Lubin-Germain N.Seghrouchni L. Tetrahedron Lett. 2002, 43: 5255 - 101
Isaac MB.Chan T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003 - 102
Wang Z.Hammond GB. J. Org. Chem. 2000, 65: 6547 - 103
Lee PH.Bang K.Lee K.Lee C.-H.Chang S. Tetrahedron Lett. 2000, 41: 7521 - 104
Lu W.Ma J.Yang Y.Chan TH. Org. Lett. 2000, 2: 3469 - 105
Miyabe H.Ueda M.Nishimura A.Naito T. Org. Lett. 2002, 4: 131 - 106
Lee PH.Sung S.-y.Lee K.Chang S. Synlett 2002, 146 - 107
Lee K.Seomoon D.Lee PH. Angew. Chem. Int. Ed. 2002, 41: 3901 ; Angew. Chem. 2002, 114, 4057 - 108
Hirashita T.Yamamura H.Kawai M.Araki S. Chem. Commun. 2001, 387 - 109
Anwar U.Grigg R.Rasparini M.Savic V.Sridharan V. Chem. Commun. 2000, 645 - 110
Anwar U.Grigg R.Sridharan V. Chem. Commun. 2000, 933 - 111
Cooper IR.Grigg R.MacLachlan WS.Thornton-Pett M.Sridharan V. Chem. Commun. 2002, 1372 - 112
Kang S.-K.Lee S.-W.Jung J.Lim Y. J. Org. Chem. 2002, 67: 4376 - 113
Yoo BW.Hwang SK.Kim DY.Choi JW.Ko JJ.Choi KI.Kim JH. Tetrahedron Lett. 2002, 43: 4813 - 114
Schick H.Ludwig R.Schwarz K.-H.Kleiner K.Kunath A. Angew. Chem., Int. Ed. Engl. 1993, 32: 1191 ; Angew. Chem. 1993, 105, 1218; - 115
Schick H.Ludwig R.Schwarz K.-H.Kleiner K.Kunath A. J. Org. Chem. 1994, 59: 3161 - 116
Lee PH.Bang K.Lee K.Sung S.-y.Chang S. Synth. Commun. 2001, 31: 3781 - 117
Araki S.Katsumura N.Kawasaki K.-i.Butsugan Y. J. Chem. Soc., Perkin Trans. 1 1991, 499 - 118
Schwarz K.-H.Kleiner K.Ludwig R.Schick H. Chem. Ber. 1993, 126: 1247 - 119
Chao L.-C.Rieke RD. J. Org. Chem. 1975, 40: 2253 - 120
Araki S.Ito H.Butsugan Y. Synth. Commun. 1988, 18: 453 - 121
Yi X.-H.Meng Y.Li C.-J. Tetrahedron Lett. 1997, 38: 4731 - 122
Johar PS.Araki S.Butsugan Y. J. Chem. Soc., Perkin Trans. 1 1992, 711 - 123
Banik BK.Ghatak A.Becker FF. J. Chem. Soc., Perkin Trans. 1 2000, 2179 - 124
Araki S.Jin S.-J.Idou Y.Butsugan Y. Bull. Chem. Soc. Jpn. 1992, 65: 1736 - 125
Takai K.Ikawa Y. Org. Lett. 2002, 4: 1727 - 126
Loh T.-P.Li X.-R. Angew. Chem., Int. Ed. Engl. 1997, 36: 980 ; Angew. Chem. 1997, 109, 1029 - 127
Augé J.Lubin-Germain N.Thiaw-Woaye A. Tetrahedron Lett. 1999, 40: 9245 - 128
Takai K.Ikawa Y.Ishii K.Kumanda M. Chem. Lett. 2002, 172 - 129
Yadav JS.Anjaneyulu S.Ahmed MM.Reddy BVS. Tetrahedron Lett. 2001, 42: 2557 - 130
Zhan Z.Zhang Y. Synth. Commun. 1998, 28: 493 - 131
Zheng Y.Bao W.Zhang Y. Synth. Commun. 1997, 27: 79 - 132
Gynane MJS.Worrall IJ. J. Organomet. Chem. 1974, 81: 329 - 133
Chan TH.Yang Y. J. Am. Chem. Soc. 1999, 121: 3228 - 135
Araki S.Butsugan Y. J. Chem. Soc., Chem. Commun. 1989, 1286 - 136
Ranu BC.Guchhait SK.Sarkar A. Chem. Commun. 1998, 2113 - 137
Ranu BC.Dutta P.Sarkar A. Tetrahedron Lett. 1998, 39: 9557 - 138
Moody CJ.Pitts MR. Synlett 1998, 1028 - 139
Pitts MR.Harrison JR.Moody CJ. J. Chem. Soc., Perkin Trans. 1 2001, 955 - 140
Banik BK.Suhendra M.Banik I.Becker FF. Synth. Commun. 2000, 30: 3745 - 141
Hutchinson I.Stevens MFG.Westwell AD. Tetrahedron Lett. 2000, 41: 425 - 142
Yoo BW.Lee SJ.Yoo BS.Choi KI.Kim JH. Synth. Commun. 2002, 32: 2489 - 143
Lee JG.Choi KI.Koh HY.Kim Y.Kang Y.Cho YS. Synthesis 2001, 81 - 144
Yadav JS.Subba Reddy BV.Srinivas R.Ramalingam T. Synlett 2000, 1447 - 145
Kim BH.Jin Y.Jun YM.Han R.Baik W.Lee BM. Tetrahedron Lett. 2000, 41: 2137 - 146
Kim BH.Cheong JW.Han R.Jun YM.Baik W.Lee BM. Synth. Commun. 2001, 31: 3577 - 147
Kang KH.Choi KI.Koh HY.Kim Y.Chung BY.Cho YS. Synth. Commun. 2001, 31: 2277 - 148
Moody CJ.Pitts MR. Synlett 1999, 1575 - 149
Harrison JR.Moody CJ.Pitts MR. Synlett 2000, 1601 - 150
Reddy GV.Rao GV.Iyengar DS. Tetrahedron Lett. 1999, 40: 3937 - 151
Yadav JS.Reddy BVS.Reddy GSKK. New J. Chem. 2000, 24: 571 - 152
Yadav JS.Madhuri C.Reddy BVS.Reddy GSKK.Sabitha G. Synth. Commun. 2002, 32: 2771 - 153
Moody CJ.Pitts MR. Synlett 1998, 1029 - 154
Das B.Srinivas KVNS. Synth. Commun. 2001, 31: 1815 - 155
Kalyanam N.Rao GV. Tetrahedron Lett. 1993, 34: 1647 - 156
Banik BK.Hackfeld L.Becker FF. Synth. Commun. 2001, 31: 1581 - 157
Jeevanandam A.Cartwright C.Ling Y.-C. Synth. Commun. 2000, 30: 3153 - 158
Yadav JS.Reddy BVS.Reddy MM. Tetrahedron Lett. 2000, 41: 2663 - 159
Ranu BC.Dutta P.Sarkar A. J. Chem. Soc., Perkin Trans. 1 1999, 1139 - 160
Park L.Keum G.Kang SB.Kim KS.Kim Y. J. Chem. Soc., Perkin Trans. 1 2000, 4462 - 161
Pena MA.Pérez I.Sestelo JP.Sarandeses LA. Chem. Commun. 2002, 2246 - 162
Chae H.Cho S.Keum G.Kang SB.Pae AN.Kim Y. Tetrahedron Lett. 2000, 41: 3899 - 163
Bao W.Zhang Y. Synlett 1996, 1187 - 164
Ranu BC.Samanta S.Guchhait SK. J. Org. Chem. 2001, 66: 4102 - 165
Ranu BC.Samanta S.Das A. Tetrahedron Lett. 2002, 43: 5993 - 166
Mineno T.Choi S.-R.Avery MA. Synlett 2002, 883 - 167
Valluri M.Mineno T.Hindupur RM.Avery MA. Tetrahedron Lett. 2001, 42: 7153 - 168
Khan FA.Dash J.Sahu N.Gupta S. Org. Lett. 2002, 4: 1015 - 169
Miyai T.Ueba M.Baba A. Synlett 1999, 182 - 170
Lim HJ.Keum G.Kang SB.Chung BY.Kim Y. Tetrahedron Lett. 1998, 39: 4367 - 171
Baek HS.Lee SJ.Yoo BW.Ko JJ.Kim SH.Kim JH. Tetrahedron Lett. 2000, 41: 8097 - 172
Ranu BC.Dutta J.Guchhait SK. Org. Lett. 2001, 3: 2603 - 173
Ranu BC.Dutta J.Guchhait SK. J. Org. Chem. 2001, 66: 5624 - 174
Yadav JS.Bandyopadhyay A.Reddy BVS. Synlett 2001, 1608 - 175
Reddy GVS.Rao GV.Iyengar DS. Synth. Commun. 2000, 30: 859
References
Podlech, J. unpublished results.
134Steurer, S.; Podlech, J. unpublished results.