Palladium-Catalyzed Equilibrium Addition of Acidic OH Groups across Dienes

Angewandte Chemie - International Edition

Volumn 42, Issue 47, 2003, Pages 5865-5868

  Utsunomiya, Masaru ^a   Kawatsura, Motoi ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Addition; Alcohols; Alkenes; Carboxylic acids; Dienes; Palladium

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; CATALYSIS; CHEMICAL BONDS; COMPLEXATION; ETHERS; OLEFINS; PHENOLS;

REVERSE ELIMINATION;

PALLADIUM;

ALKADIENE; ALLYL COMPOUND; ETHER DERIVATIVE; HYDROXYL GROUP; PALLADIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; EQUILIBRIUM CONSTANT; LOW TEMPERATURE; REACTION ANALYSIS;

ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CYCLOHEXANES; CYCLOHEXENES; ESTERS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; PHENOL; PHOSPHINES;

EID: 0348050486     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352621     Document Type: Article

References (20)

1. S. A. Godleski, B. M. Trost, I. Fleming in Comprehensive Organic Synthesis, Vol. 4 (Eds.: S. A. Godleski, B. M. Trost, I. Fleming), Pergamon, New York, 1991, p. 585.
2. L. J. GooßBen, Angew. Chem. 2002, 114, 3929; Angew. Chem. Int. Ed. 2002, 41, 3775.
3. L. J. GooßBen, Angew. Chem. 2002, 114, 3929; Angew. Chem. Int. Ed. 2002, 41, 3775.
4. T. Pei, R. A. Widenhoefer, J. Am. Chem. Soc. 2001, 123, 11290.
5. B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438.
6. P. W. Jolly, N. Kokel, Synthesis 1990, 771.
7. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675.
8. M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 5608.
9. M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546.
10. W. Keim, A. Behr, M. Roper in Comprehensive Organametallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone), Pergamon, Oxford, 1982, p. 371.
11. J. Tsuji, Acc. Chem. Res. 1973, 6, 8.
12. R. Jackstell, A. Frisch, M. Beller, D. Rottger, M. Malaun, B. Bildstein, J. Mol. Catal. A 2002, 185, 105.
13. J. E. Backvall, Adv. Met.-Org. Chem. 1989, 1,135.
14. For an example of a nickel-catalyzed addition of phenol to for a mixture of telomerization and 1:1 addition products, see: V. J. Beger, C. H. Duschek, G. W. Füllbier, J. Prakt. Chem. 1974, 316, 26.
15. O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366.
16. J. Pawalas, Y. Nakano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669.
17. C. F. J. Barnard, M. J. H. Russell in Comprehensive Organometallic Chemistry, Vol. 5 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1987, p. 1101.
18. DPPE=1,2-Bis(diphenylphosphino)ethane, DPPF=1,1′ -Bis(-diphenylphosphino)ferrocene, BINAP=2,2′ -Bis(diphenylphosphino)-1,1′-binaphthyl, Xantphos=9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene
19. See supporting information for data.
20. J. F. Izquierdo, F. Cunill, M. Vila, M. Iborra, J. Tejero, Ind. Eng. Chem. Res. 1994, 33, 2830.