Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols

Angewandte Chemie - International Edition

Volumn 44, Issue 42, 2005, Pages 6913-6915

  Kwon, Min Serk ^a   Kim, Namdu ^a   Seo, Seong Hyeok ^a   Park, In Soo ^a   Cheedrala, Ravi Kumar ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Alkylation; Aluminum; C C coupling; Heterogeneous catalysis; Palladium

Indexed keywords

ALKYLATION; ALUMINUM; ALUMINUM COMPOUNDS; CATALYSIS; KETONES; PALLADIUM;

ALUMINUM HYDROXIDE; AROMATIC KETONES; C-C COUPLING; PALLADIUM NANOPARTICLES;

CATALYSTS;

ALCOHOL DERIVATIVE; KETONE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALKYLATION; CATALYSIS; KETONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 27544475113     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502422     Document Type: Article

References (19)

1. a) D. Caine in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1-63;
2. b) S. Carrettin, J. Guzman, A. Corma, Angew. Chem. 2005, 117, 2282-2285;
3. Angew. Chem. Int. Ed. 2005, 44, 2242-2245;
4. c) Modern Carbonyl Chemistry (Ed.: J. Otera), Wiley-VCH, Weinheim, 2000.
5. a) C. S. Cho, B. T. Kim, M. J. Lee, T.-J. Kim, S. C. Shim, Angew. Chem. 2001, 113, 984-986;
6. Angew. Chem. Int. Ed. 2001, 40, 958-960;
7. b) C. S. Cho, B. T. Kim, T.-J. Kim, S. C. Shim, J. Org. Chem. 2001, 66, 9020-9022;
8. c) C. S. Cho, B. T. Kim, T.-J. Kim, S. C. Shim, Tetrahedron Lett. 2002, 43, 7987-7989;
9. d) C. S. Cho, B. T. Kim, H.-S. Kim, T.-J. Kim, S. C. Shim, Organometallics 2003, 22, 3609-3610;
10. e) K. Taguchi, H. Nakagawa, T. Hirabayashi, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2004, 126, 72-73;
11. f) R. Martínez, G.-J. Brand, D.-J. Ramón, M. Yus, Tetrahedron Lett. 2005, 46, 3683-3686.
12. K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 5662-5663.
13. M. S. Kwon, N. Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077-1079.
14. 4 was used.
15. 2 is used as the catalyst; see ref. [2f].
16. Pregnenolone is a main precursor of steroid hormones: K. Tsutsui, H. Sakamoto, K. Ukena, J. Steroid Biochem. Mol. Biol. 2003, 85, 311-321.
17. 1H NMR spectroscopic analysis, no diastereomer of the major coupling product was formed in significant yield.
18. Palladium was not detected in the filtrate with inductively coupled plasma (ICP) analysis.
19. The NMR spectroscopic data for the coupling products shown in Table 3 and the experimental procedures for the preparation of 1, E-1,3-diphenyl-2-propen- 1-one, and 21-benzylpregnenolone are contained in the Supporting Information.