4-Bromo-3-formyl-1,2-dihydronaphthalenes undergo Suzuki cross coupling and Wittig olefination reaction in a one pot procedure. The trienes obtained can be cyclised thermally under concomitant dehydrogenation to dihydrophenanthrothiophenes and dihydrophenanthro[1]benzothiophenes. An X-ray crystal structural analysis was carried out for ethyl (E)-3-[1-(1-benzothiophen-3-yl)-3,4-dihydro-2-naphthyl]propenoate.
ThiemannT., GehrckeB., and de MeijereA., Synlett, 1993, 483; (c) for a review, see: C.M. Marson, Tetrahedron, 1992, 48, 3659.
9.
(a) MiyauraN., and SuzukiA., Chem. Rev., 1995, 95, 2457.
10.
SuzukiA., J. Organomet. Chem., 1999, 576, 147.
11.
For the use of (Ph3P)2PdCl2 in Suzuki cross-coupling reactions in the synthesis of biaryls and bishetaryls, see: (a) SuzukiA., Cross-Coupling of Organoboron Compounds with Organic Halides In Metal Catalysed Cross-Coupling Reactions, DiederichF., and StangP. J., (eds), VCH-Wiley, pp. 49.
12.
MelucciM., BarbarellaG., and SotgiuG., J. Org. Chem., 2002, 67, 8877.
13.
For the classification of phosphoranes into stabilized, semi-stabilized and non-stabilized, see: FurhopJ., and PenzlinG., Organic Synthesis–Concepts, Methods and Starting Materials, VCH, Weinheim, 1983, pp. 26.
14.
WatanabeM., MatakaS., and ThiemannT., Steroids, in press.
15.
DesimoniG., FaitaG., GuidettiS., and RighettiP. P., Eur. J. Org. Chem., 1999, 1921.
16.
for a review, see: ThiemannT., ArimaK., and MatakaS., Rep. Inst. Adv. Mat. Kyushu Univ., 2000, 14, 37.
17.
(a) VoigtK., von ZezschwitzP., RosauerK., LanskyA., and de MeijereA., Eur. J. Org. Chem., 1998, 1521.
18.
von ZezschwitzP., PetryF., and de MeijereA., Chem. Eur. J., 2001, 7, 4035.
19.
GilchristT.L., and SummersellR. J., J. Chem. Soc., Perkin Trans. 1, 1988, 2595.
20.
(a) RamirezF., and DershowitzS., J. Org. Chem., 1957, 22, 41.
21.
ConsidineWm. J., J. Org. Chem., 1962, 27, 647.
22.
Autorenkollektiv, Organikum – Organisch-chemisches Grundpraktikum, VEB Deutscher Verlag der Wissenschaften, Berlin1977, pp. 261.
23.
AltomareA., BurlaM. C., CamalliM., CascaranoG., GiacovazzoC., GuigliardiC., MoliterniA. G. G., PolidoriG., and SpagnaR., J. Appl. Cryst., 1999, 32, 115.
24.
WatkinD.J., ProutC. K., CarruthersJ. R., and BetteridgeP. W., CRYSTALS, Issue 10, Chemical Crystallography Laboratory, University of Oxford, England, 1996.
