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Synthesis 2006(20): 3478-3484
DOI: 10.1055/s-2006-950239
DOI: 10.1055/s-2006-950239
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis, Cross-Coupling, and Anionic Cyclization of ortho-Substituted Naphthaleneboronic Esters
Further Information
Received
3 February 2006
Publication Date:
10 October 2006 (online)
Publication History
Publication Date:
10 October 2006 (online)
Abstract
1-Fluoro-, 1-chloro- and 1-cyanonaphthalene were lithiated and then borylated at the 2-position. The 1-substituted naphthaleneboronic esters were cross-coupled with aryl halides to give 2-aryl-1-fluoro-, 2-aryl-1-chloro- and 2-aryl-1-cyanonaphthalenes. The 2-aryl-1-cyano- and 2-aryl-1-fluoronaphthalenes were reacted with n-butyllithium or lithium morpholide to give new benzophenanthridine derivatives.
Key words
lithiation - cross-coupling - aromatic substitution - cyclization - fused-ring system
- 1
Miyaura N. In Advances in Metal Organic Chemistry Vol. 6:Liebeskind LS. Jai Press Inc; Stamford: 1998. p.187 - 2
Suzuki A. J. Organomet. Chem. 1999, 576: 147 - 3
Snieckus V. In Metal Catalyzed Cross-Coupling Reactionsde Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. p.761 - 4
Batey RA.Quach TD.Shen M.Thadani AN.Smil DV.Li S.-W.MacKay DB. Pure Appl. Chem. 2002, 74: 43 - 5
Hayashi T. Pure Appl. Chem. 2004, 76: 465 - 6
Bumagin NA.Korolev DN. Tetrahedron Lett. 1999, 40: 3057 - 7
Haddach M.McCarthy JR. Tetrahedron Lett. 1999, 40: 3109 - 8
Liebeskind LS.Srogl J. J. Am. Chem. Soc. 2000, 122: 11260 - 9
Gooßen LJ.Ghosh K. Angew. Chem. Int. Ed. 2001, 40: 3458 - 10
Gooßen LJ.Ghosh K. Chem. Commun. 2001, 2084 - 11
Gooßen LJ.Winkel L.Döhring A.Ghosh K.Paetzold J. Synlett 2002, 1237 - 12
Kakino R.Narahashi H.Shimizu I.Yamamoto A. Bull. Chem. Soc. Jpn. 2002, 75: 1333 - 13
Urawa Y.Ogura K. Tetrahedron Lett. 2003, 44: 271 - 14
Oh CH.Reddy VR. Tetrahedron Lett. 2004, 45: 8545 - 15
Duan Y.-Z.Deng M.-Z. Synlett 2005, 355 - 16
Ishiyama T.Kizaki H.Hayashi T.Suzuki A.Miyaura N. J. Org. Chem. 1998, 63: 4726 - 17
Andrus MB.Ma Y.Zang Y.Song C. Tetrahedron Lett. 2002, 43: 9137 - 18
Ma Y.Song C.Chai Q.Ma C.Andrus MB. Synthesis 2003, 2886 - 19
Lysén M.Kelleher S.Begtrup M.Kristensen JL. J. Org. Chem. 2005, 70: 5342 - 20
Thiebes C.Prakash GKS.Petasis NA.Olah GA. Synlett 1998, 141 - 21
Szumigala RH.Devine PN.Gauthier DR.Volante RP. J. Org. Chem. 2004, 69: 566 - 22
Webb KS.Levy D. Tetrahedron Lett. 1995, 36: 5117 - 23
Maleczka RE.Shi F.Holmes D.Smith MR.
J. Am. Chem. Soc. 2003, 125: 7792 - 24
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 - 25
Quach TD.Batey RA. Org. Lett. 2003, 5: 4397 - 26
Antilla JC.Buchwald SL. Org. Lett. 2001, 3: 2077 - 27
Lan J.-B.Zhang G.-L.Yu X.-Q.You J.-S.Chen L.Yan M.Xie R.-G. Synlett 2004, 1095 - 28
Kristensen JL.Lysén M.Vedsø P.Begtrup M. Org. Lett. 2001, 3: 1435 - 29
Kristensen JL.Lysén M.Vedsø P.Begtrup M. Org. Synth. 2004, 81: 134 - 30
Lysén M.Hansen HM.Kristensen JL.Begtrup M. J. Org. Chem. 2006, 71: 2518 - 32
Fraser RR.Savard S. Can. J. Chem. 1986, 64: 621 - 33
Schlosser M.Rausis T. Eur. J. Org. Chem. 2002, 3351 - 34
Gilman H.Crounse NN.Massie SP.Benkeser RA.Spatz SM. J. Am. Chem. Soc. 1945, 67: 2106 - 35
Sauer J.Huisgen R.Hauser A. Chem. Ber. 1958, 91: 1461 - 36
Husigen R.Sauer J.Hauser A. Chem. Ber. 1958, 91: 2367 - 37
Urner RS.Bergstrom EW. J. Am. Chem. Soc. 1945, 67: 2108 - 38
Stanforth SP. Tetrahedron 1998, 54: 263 - 39
Hagen S.Hopf H. In Carbon Rich Compounds IMeijere A. Springer-Verlag; Berlin: 1998. p.45 - 40
Bringmann G.Walter R.Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977 - 41
Cepanec I. Synthesis of Biaryls Elsevier; Amsterdam: 2004. - 42
Holloway HE.Nauman RV.Warton JH. J. Phys. Chem. 1968, 72: 4468 - 43
Boyer JH. J. Chem. Soc., Chem. Commun. 1977, 855 - 44
Aversa MC.Cum G.Gianetto P.Romeo G. J. Chem. Res., Synop. 1978, 292 - 45
Lysén M.Kristensen JL.Vedsø P.Begtrup M. Org. Lett. 2002, 4: 257 - 46
Hansen HM.Lysén M.Kristensen JL.Begtrup M. Tetrahedron 2005, 61: 9955 - 47
Nyangulu JM.Hargreaves SL.Sharples SL.MacKay SP.Waigh RD.Duval O.Mberu EK.Watkins WM. Bioorg. Med. Chem. Lett. 2005, 15: 2007 - 48
Razafimbelo J.Baudouin G.Tillequin F.Renard P.Léonce S.Pierre A.Atassi G. Chem. Pharm. Bull. 1998, 46: 34 - 49
Martinez R.Chacon-Garcia L. Curr. Med. Chem. 2005, 12: 127 - 50
Lynch MA.Duval O.Sukhanova A.MacKay SP.Waigh RD.Nabiev I. Bioorg. Med. Chem. Lett. 2001, 11: 2643 - 51
Siddiqui MA.Snieckus V. Tetrahedron Lett. 1988, 29: 5463 - 52
Kock I.Clement B. Synthesis 2005, 1052 - 53
Clayden J.Frampton CS.McCarthy C.Westlund N. Tetrahedron 1999, 55: 14161 - 54
Hegedus LS. In Organometallics in SynthesisSchlosser M. Wiley; New York: 1995. p.448
References
Neopentylglycol = 2,2-dimethylpropane-1,3-diol.