Heck reactions without salt formation: Aromatic carboxylic anhydrides as arylating agents

Angewandte Chemie - International Edition

Volumn 37, Issue 5, 1998, Pages 662-664

  Stephan, Massoud S ^a   Teunissen, Antonius J J M ^a   Verzijl, Gerard K M ^a   De Vries, Johannes G ^a  

^a DSM RESEARCH   (Netherlands)

Author keywords

Alkenes; Anhydrides; Arenes; C C coupling; Homogeneous catalysis

Indexed keywords

EID: 0031925015     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980316)37:5<662::AID-ANIE662>3.0.CO;2-0     Document Type: Article

References (24)

1. a) R. F. Heck, Org. React. 1982, 27-390, 345;
2. b) R. F. Heck in Comprehensive Organic Synthesis, Vol.4, (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, 833-863;
3. c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
4. c) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
5. d) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7;
6. e) J. Tsuji, Palladium Reagents and Catalysts-Innovations in Organic Synthesis, Wiley, Chichester, UK, 1995.
7. a) W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1847;
8. a) W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1847;
9. b) W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357-1364.
10. The rhodium-catalyzed benzoylation of styrene with benzoic anhydride has been reported: K. Kokubo, M. Miura, M. Nomura, Organometallics 1995, 14, 4521-4524.
11. T. Jeffery, Tetrahedron 1996, 52, 10113-10130, and references herein.
12. Halides are not a prerequisite for the formation of clusters aided by tetraalkylammonium salts: M. T. Reetz, S. A. Quaiser, Angew. Chem. 1995, 107, 2461-2463; Angew. Chem. Int. Ed. Engl. 1995, 34, 2240-2241.
13. Halides are not a prerequisite for the formation of clusters aided by tetraalkylammonium salts: M. T. Reetz, S. A. Quaiser, Angew. Chem. 1995, 107, 2461-2463; Angew. Chem. Int. Ed. Engl. 1995, 34, 2240-2241.
14. a) M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257-259;
15. b) M. T. Reetz, R. Breinbauer, K. Wanninger, Tetrahedron Lett. 1996, 37, 4499-4502.
16. The role of chloride-ligated palladium phosphane complexes in oxidative addition reactions has been discussed: a) C. Amatore, M. Azzabi, A. Jutand, J. Am. Chem. Soc. 1991, 113, 8375-8384; b) C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc. 1993, 115, 9531-9541.
17. The role of chloride-ligated palladium phosphane complexes in oxidative addition reactions has been discussed: a) C. Amatore, M. Azzabi, A. Jutand, J. Am. Chem. Soc. 1991, 113, 8375-8384; b) C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc. 1993, 115, 9531-9541.
18. 2 to Pd black in NMP solutions at room temperature. This might be due to amine impurities in the solvent.
19. K. Nagayama, F. Kawataka, M. Sakamoto, I. Shimizu , A. Yamamoto, Chem. Lett. 1995, 367-368.
20. -).
21. For a discussion on the factors influencing the stereochemical and regiochemical outcome of Heck reactions, see refs. [1b, 1c] and a) A. Spencer, J. Organomet. Chem. 1982, 240, 209-216; b) C.-M. Andersson, A. Hallberg, J. Org. Chem. 1988, 53, 235-239.
22. For a discussion on the factors influencing the stereochemical and regiochemical outcome of Heck reactions, see refs. [1b, 1c] and a) A. Spencer, J. Organomet. Chem. 1982, 240, 209-216; b) C.-M. Andersson, A. Hallberg, J. Org. Chem. 1988, 53, 235-239.
23. M. Beller, T. H. Riermeier, Tetrahedron Lett. 1996, 37, 6535-6538.
24. 2 and 0.4 mol % halide is also possible without reducing the yield; reaction times increase to 3-5 h.