New methods for the synthesis of ArPdL2I (L = tertiary phosphine) complexes

Organometallics

Volumn 15, Issue 17, 1996, Pages 3708-3716

  Wallow, Thomas I ^b   Goodson, Felix E ^c   Novak, Bruce M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b LUCENT TECHNOLOGIES   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000047592     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9602567     Document Type: Article

References (89)

1. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
2. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
3. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
4. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
5. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
6. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
7. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
8. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
9. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
10. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
11. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
12. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
13. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
14. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
15. For selected reviews, compilations, and monographs, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Negishi, E. I. Acc. Chem. Res. 1982, 15, 340. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. (d) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic: London, 1985. (e) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (g) Beletskaya, I. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 39, 2013. (h) Undheim, K.; Benneche, T. Heterocycles 1990, 30, 2. (i) Suzuki, A. Pure Appl. Chem. 1991, 63, 419. (j) Mitchell, T. N. Synthesis 1992, 803. (k) Hegedus, L. S. J. Organomet. Chem. 1993, 457, 167. (l) Undheim, K.; Benneche, T. Acta Chem. Scand. 1990, 47, 102. (m) Martin, A. R.; Yang, Y. H. Acta Chem. Scand. 1993, 47, 221. (n) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (o) Hegedus, L. S. J. Organomet. Chem. 1994, 477, 269.
16. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
17. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
18. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
19. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
20. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
21. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
22. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
23. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
24. 4 or reaction mixtures containing excess phosphines. Use of these systems is ubiquitous; see reviews in ref 1. Catalyst stability in the presence of excess phosphines is sometimes invoked: some degree of catalyst tailoring to complement the reactivity of a given substrate appears to be necessary in instances when sterically hindered or complex multifunctional substrates are used. Control of Pd:ligand stoichiometry is frequently accomplished by generating catalytic species in situ. For comprehensive discussions of subtleties that pertain to such processes as well as extensive compilations of methods employing in-situ generated catalysts; see: (i) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375. (j) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
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