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(2): 173-189
DOI: 10.1055/s-0030-1258305
DOI: 10.1055/s-0030-1258305
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Nitrogen-Centered Radical Scavengers
Weitere Informationen
Received
26 August 2010
Publikationsdatum:
18. Oktober 2010 (online)
Publikationsverlauf
Publikationsdatum:
18. Oktober 2010 (online)
Abstract
As reactants in radical reactions, nitrogen-centered scavengers can offer valuable alternatives to ionic methods regarding the synthesis of nitrogen-containing compounds. In this review article, we present developments, scope, limitations and future challenges in this field of radical chemistry.
1 Introduction
2 Alkyl Azides
3 Sulfonyl Azides
3.1 Reactions with Alkyl Radicals
3.2 Functionalization of Alkenes
3.3 Diastereoselective Reactions
3.4 Natural Product Synthesis
4 Arenediazonium Salts
4.1 Reactions with Alkyl Radicals
4.2 Functionalization of Alkenes
4.3 Functionalization of Arenes
5 Azo Compounds
5.1 Intramolecular Addition
5.2 Diazirines
5.3 Azo Dicarboxylates
6 Nitrogen Monoxide and Synthetic Equivalents
6.1 Nitrogen Monoxide
6.2 Thionitrosyl Esters
6.3 Alkyl Nitrites
7 Imines
7.1 Intramolecular Addition
7.2 Stannylimines
8 Hydrazines
9 Conclusion
Key words
radicals - radical reaction - azides - azo compounds - imines
- 1
Kim S.Joe GH.Do JY. J. Am. Chem. Soc. 1993, 115: 3328 - 2
Kim S.Joe GH.Do JY. J. Am. Chem. Soc. 1994, 116: 5521 - 3
Kim S.Kee IS.Lee SJ. J. Am. Chem. Soc. 1991, 113: 9882 - 4
Kizil M.Murphy JA. J. Chem. Soc., Chem. Commun. 1995, 1409 - 5
Roberts BP.Winter JN. J. Chem. Soc., Perkin Trans. 2 1979, 1353 - 6
Roberts BP.Dang H.-S. J. Chem. Soc., Perkin Trans. 1 1996, 1493 - 7
Renaud P.Ollivier C. J. Am. Chem. Soc. 2000, 122: 6496 - 8
Renaud P.Ollivier C. J. Am. Chem. Soc. 2001, 123: 4717 - 9
Porter NA.Masterson DS. Org. Lett. 2002, 4: 4253 - 10
Barton DHR.Crich D.Motherwell WB. J. Chem. Soc., Chem. Commun. 1983, 939 - 11
Kim S.Lim CJ.Song S.-E.Kang H.-Y. Synlett 2001, 688 - 12
Kim S.Lim CJ.Song S.-E.Kang H.-Y. Chem. Commun. 2001, 1410 - 13
Barton DHR.Hervé Y.Potier P.Thierry J. Tetrahedron 1988, 44: 5479 - 14
Renaud P.Nyfeler E. Org. Lett. 2008, 10: 985 - 15
Renaud P.Ollivier C.Panchaud P. Angew. Chem. Int. Ed. 2002, 41: 3460 ; Angew. Chem. 2002, 114, 3610 - 16
Renaud P.Panchaud P. J. Org. Chem. 2004, 69: 3205 - 17
Renaud P.Panchaud P. Adv. Synth. Catal. 2004, 346: 925 - 18
Renaud P.Mantrand N. Tetrahedron 2008, 64: 11860 - 19
Landais Y.Chabaud L.Renaud P. Org. Lett. 2002, 4: 4257 - 20
Renaud P.Chabaud L.Landais Y.Robert F.Castet F.Lucarini M.Schenk K. Chem. Eur. J. 2008, 14: 2744 - 21
Renaud P.Cren S.Schär P.Schenk K. J. Org. Chem. 2009, 74: 2942 - 22
Renaud P.Panchaud P.Chabaud L.Landais Y.Ollivier C.Zigmantas S. Chem. Eur. J. 2004, 10: 3606 - 23
Renaud P.Panchaud P.Ollivier C.Zigmantas S. J. Org. Chem. 2004, 69: 2755 - 24
Renaud P.Chabaud L.Landais Y. Org. Lett. 2005, 7: 2587 - 25
Renaud P.Schär P. Org. Lett. 2006, 8: 1569 - 26
Renaud P.Kapat A.Nyfeler E.Giuffredi GT. J. Am. Chem. Soc. 2009, 131: 17746 - 27
Al Adel I.Salami BA.Levisalles J.Rudler H. Bull. Soc. Chim. Fr. 1976, 934 - 28
Citterio A.Minisci F. J. Org. Chem. 1982, 47: 1759 - 29
Minisci F.Coppa F.Fontana F.Pianese G.Zhao L. J. Org. Chem. 1992, 57: 3929 - 30
Meerwein H.Büchner E.Emster K. J. Prakt. Chem. 1939, 152: 237 -
31a
Rondestvedt CS. Org. React. 1976, 24: 225 -
31b
Heinrich MR. Chem. Eur. J. 2009, 15: 820 - 32
Citterio A.Minisoi F.Albinati A.Bruokner S. Tetrahedron Lett. 1980, 21: 2909 - 33
Citterio A.Minisci F.Vismara E. J. Org. Chem. 1982, 47: 81 - 34
Giese B. Angew. Chem. Int. Ed. 1983, 22: 753 ; Angew. Chem. 1983, 95, 771 - 35
Citterio A.Ramperti M.Vismara E. J. Heterocycl. Chem. 1981, 18: 763 - 36
Minisci F.Fontana F.Vismara E. Gazz. Chim. Ital. 1993, 123: 9 - 37
Merkushev EB. Synthesis 1988, 923 - 38
Garden SJ.Avila DV.Beckwith ALJ.Bowry VW.Ingold KU.Lusztyk J. J. Org. Chem. 1996, 61: 805 - 39
Heinrich MR.Blank O.Wölfel S. Org. Lett. 2006, 8: 3323 - 40
Heinrich MR.Blank O.Wetzel A. J. Org. Chem. 2007, 72: 476 - 41
Heinrich MR.Blank O.Wetzel A.Ullrich D. Eur. J. Org. Chem. 2008, 3179 - 42
Heinrich MR.Blank O. Eur. J. Org. Chem. 2006, 4331 - 43
Heinrich MR.Blank O.Raschke N. Tetrahedron Lett. 2010, 51: 1758 - 44
Brunner H.Blüchel C.Doyle MP. J. Organomet. Chem. 1997, 541: 89 - 45
Heinrich MR.Blank O.Wetzel A. Synlett 2006, 3352 - 46
Wetzel A.Pratsch G.Kolb R.Heinrich MR. Chem. Eur. J. 2010, 16: 2547 - 47
Wetzel A.Ehrhardt V.Heinrich MR. Angew. Chem. 2008, 120: 9270 ; Angew. Chem. Int. Ed. 2008, 47, 9130 - 48
Beckwith ALJ.Wang S.Warkentin J. J. Am. Chem. Soc. 1987, 109: 5289 - 49
Wang SF.Mathew L.Warkentin J. J. Am. Chem. Soc. 1988, 110: 7235 - 50
Kunka CPA.Warkentin J. Can. J. Chem. 1990, 68: 5759 - 51
Alberti A.Bedogni N.Benaglia M.Leardini R.Nanni D.Pedulli GF.Tundo A.Zanardi G. J. Org. Chem. 1992, 57: 607 - 52
Leardini R.Lucarini M.Nanni A.Nanni D.Pedulli GF.Tundo A.Zanardi G. J. Org. Chem. 1993, 58: 2419 - 53
Barton DHR.Jaszberenyi JC.Theodorakis EA. J. Am. Chem. Soc. 1992, 114: 5904 - 54
Barton DHR.Jaszberenyi JS.Theodorakis EA.Reibenspies JH. J. Am. Chem. Soc. 1993, 115: 8050 -
55a
Alder K.Pascher F.Schmitz A. Ber. Dtsch. Chem. Ges. B 1943, 76: 27 -
55b
Alder K.Noble T. Ber. Dtsch. Chem. Ges. B 1943, 76: 64 - 56
Horner L.Naumann W. Liebigs Ann. Chem. 1964, 587: 81 - 57
Huisgen R.Pohl H. Chem. Ber. 1960, 93: 527 - 58
Shah A.George MV. Tetrahedron 1971, 27: 1291 - 59
Baigrie BD.Cadogan JIG.Sharp JT. J. Chem. Soc., Perkin Trans. 1 1975, 1029 - 60
Okamoto T.Oka S. J. Chem. Soc., Chem. Commun. 1984, 289 - 61
Halpern J. Science 1985, 227: 869 - 62
Patel VF.Pattenden G. Tetrahedron Lett. 1987, 28: 1451 - 63
Ghosez A.Göbel T.Giese B. Chem. Ber. 1988, 121: 1807 - 64
Veit A.Giese B. Synlett 1990, 166 - 65
Girard P.Guillot N.Motherwell WB.Potier P. J. Chem. Soc., Chem. Commun. 1995, 2385 - 66
Girard P.Guillot N.Motherwell WB.Hay-Motherwell RS.Potier P. Tetrahedron 1999, 55: 3573 - 67
Barton DHR. Pure Appl. Chem. 1968, 1 -
68a
Barton DHR.Beaton JM.Geller LE.Pechet MM. J. Am. Chem. Soc. 1960, 82: 2640 -
68b
Barton DHR.Beaton JM.Geller LE.Pechet MM. J. Am. Chem. Soc. 1961, 83: 4076 - 69
Akhtar M.Barton DHR.Sammes PG. J. Am. Chem. Soc. 1964, 86: 3394 - 70
Kizil M.Murphy JA. Tetrahedron 1997, 53: 16847 - 71
Takano S.Suzuki M.Kijima A.Ogasawara K. Chem. Lett. 1990, 315 -
72a
Tomaszewski MJ.Warkentin J. Tetrahedron Lett. 1992, 33: 2123 -
72b
Gioanola M.Leardini R.Nanni D.Pareschi P.Zanardi G. Tetrahedron 1995, 51: 2039 -
73a
Bowman WR.Stephenson PT.Terrett NK.Young AR. Tetrahedron Lett. 1994, 35: 6369 -
73b
Bowman WR.Stephenson PT.Terrett NK.Young AR. Tetrahedron 1995, 51: 7959 - 74
Han O.Frey PA. J. Am. Chem. Soc. 1990, 112: 8982 - 75
Ryu I.Matsu K.Minakata S.Komatsu M. J. Am. Chem. Soc. 1998, 120: 5838 - 76
Tojino M.Otsuka N.Fukuyama T.Matsubara H.Ryu I. J. Am. Chem. Soc. 2006, 128: 7712 - 77
Viswanathan R.Prabhakaran EN.Plotkin MA.Johnston JN. J. Am. Chem. Soc. 2003, 125: 163 - 78
McClure CK.Kiessling AJ.Link JS. Tetrahedron 1998, 54: 7121 - 79
Viswanathan R.Smith CR.Prabhakaran EN.Johnston JN. J. Org. Chem. 2008, 73: 3040 -
80a
Pastori N.Greco C.Clerici A.Punta C.Porta O. Org. Lett. 2010, 12: 3898 -
80b
Clerici A.Ghilardi A.Pastori N.Punta C.Porta O. Org. Lett. 2008, 10: 5063 -
80c
Cannella R.Clerici A.Panzeri W.Pastori N.Punta C.Porta O. J. Am. Chem. Soc. 2006, 128: 5358 -
80d
Cannella R.Clerici A.Pastori N.Regolini E.Porta O. Org. Lett. 2005, 7: 645 - 81
Lamas C.-M.Vaillard SE.Wibbeling B.Studer A. Org. Lett. 2010, 12: 2072 - 82
Barton DHR.Le Greneur S.Motherwell WB. Tetrahedron Lett. 1983, 24: 1601 - 83
Tang Q.Zhang C.Luo M. J. Am. Chem. Soc. 2008, 130: 5840