Palladium-catalyzed hydrostannylations of highly hindered acetylenes in hexane

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5737-5739

  Semmelhack, M F ^a   Hooley, Richard J ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKENE DERIVATIVE; HEXANE; PALLADIUM; PHOSPHINE; SOLVENT;

ADDITION REACTION; ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DIMERIZATION; HYDROGENATION; HYDROSTANNYLATION; REACTION TIME; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0037828820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01327-3     Document Type: Article

References (13)

1. Pereyre M., Quintard J.-P., Rahm A. Tin in Organic Synthesis. 1987;Butterworth, London.
2. Davies A.G. Organotin Chemistry. 1997;VCH, Weinheim, Germany.
3. Smith N.D., Mancuso J., Lautens M. Chem. Rev. 100:2000;3257.
4. Betzer J.-F., Delaloge F., Muller B., Pancrazi A., Prunet J. J. Org. Chem. 62:1997;7768.
5. Hydrostannylation of an analog of 1 with a free hydroxyl and R=o-bromophenyl in THF was successful: Liron F., Le Garrec P., Alami M. Synlett. 2:1999;246.
6. For a discussion of the pathways and detection of intermediates, see: Trebbe R., Schager F., Goddard R., Pörschke K.-R. Organometallics. 19:2000;521.
7. As noted in a review (Ref. 1c), little exploration of the solvent effects have been reported; for an example with internal aryl alkynes, see Ref. 3. Hexane was not employed in this study; the emphasis was on regioselectivity.
8. In principle, the counter ion on the Pd(II) should not affect the reaction, since the Pd(II) is reduced to Pd(0) as the initiation step. Again, the issue has been little studied.
9. 3Sn moiety. The vinyl methyl group was not enhanced.
10. (a) Greeves, N.; Torode, J. S. Synlett 1994, 537
11. (b) See also Ref. 3.
12. For discussion and leading references, see: Moloy K.G., Petersen J.L. J. Am. Chem. Soc. 117:1995;7696.
13. Chelating diphosphines have been used with modest success in hydrostannylation of internal aryl alkynes: see Ref. 3.