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Volumn 58, Issue 44, 2002, Pages 9007-9018

Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes: Sonogashira coupling vs cyclic carbopalladation

Author keywords

Alkynes; Aryl halides; Coupling reactions; Cyclisation

Indexed keywords

1 (2 PROPYNYLIDENE) 2,3 DIHYDRO 1H INDENE; 1H,3H BENZ[DE]ISOCHROMENE; 4 (2 PROPYNYLIDENE) 3,4 DIHYDRO 1H ISOCHROMENE; ACENAPHTHENE; ALKENE DERIVATIVE; ALKYNE; CHROMENE DERIVATIVE; COPPER; INDENE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM; PHENYL ALKYNE; PHENYL IODIDE; SOLVENT; UNCLASSIFIED DRUG;

EID: 0037191024     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01154-7     Document Type: Article
Times cited : (23)

References (10)
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    • . For reviews on Sonogashira coupling under Pd(0)/Cu(I) catalysis, see: (a) Brandsma L. Preparative Acetylenic Chemistry. 2nd ed. 1988;Elsevier, Amsterdam, (b) Sonogashira K. Trost B.M., Fleming I., Paquette L.A., Comprehensive Organic Synthesis. Vol. 3:1991;521 Pergamon, Oxford. Chapter 2.4 (c) Winterfeldt E. Scheffold R., Modern Synthetic Methods. 1992;103 VCH, Weinheim, (d) Rossi R., Carpita A., Bellina F. Org. Prep. Proc. Int. 27:1995;127 (e) Farina V. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;162 Pergamon, Oxford. Chapter 3.4 (f) Geisler H. Beller M., Bolm C., Transition Metals for Organic Synthesis. Vol. 1:1998;158 Wiley-VCH, Weinheim. Chapter 2.10 (g) Sonogashira K. Diederich F., Stang P.J., Metal-catalyzed Cross-coupling Reactions. Vol. 5:1998;203 Wiley-VCH, Weinheim.
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    • . For examples of Sonogashira reaction without CuI as a co-catalyst, see: (a) Chen Q.-Y., Yang Z.-Y. Tetrahedron Lett. 27:1986;1171 (b) Alami M., Ferri F., Linstrumelle G. Tetrahedron Lett. 34:1993;6403 (c) Böhm V.P.W., Herrmann W.A. Eur. J. Org. Chem. 2000;3679. See also Ref. 3.
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    • We are aware that pentacoordinated anionic Pd(0) and Pd(II) intermediates may be involved instead of the simplified structures outlined in Scheme 4
    • . For recent discussion on the general mechanism of Pd-catalysed Heck and cross-coupling reactions, see: Amatore C., Jutand A. Acc. Chem. Res. 33:2000;314. We are aware that pentacoordinated anionic Pd(0) and Pd(II) intermediates may be involved instead of the simplified structures outlined in Scheme 4.
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    • Alternatively, an insertion into the aryl C-H bond in G ( Scheme 4 ) to form a palladium(IV) intermediate followed by proton abstraction by a base to give the palladacycle I may take place as discussed in Ref. 8a-c,e,f,h-k
    • Alternatively, an insertion into the aryl C-H bond in G ( Scheme 4 ) to form a palladium(IV) intermediate followed by proton abstraction by a base to give the palladacycle I may take place as discussed in Ref. 8a-c,e,f,h-k.


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