A general study of [(η5-Cp′)2Ti(η 2-Me3SiC2SiMe3)]-catalyzed hydroamination of terminal alkynes: Regioselective formation of Markovnikov and anti-Markovnikov products and mechanistic explanation (Cp′=C (5)H(5), C(5)H(4)Et, C(5)Me(5))

Chemistry - A European Journal

Volumn 10, Issue 10, 2004, Pages 2409-2420

  Tillack, Annegret ^a   Jiao, Haijun ^a   Castro, Ivette Garcia ^a   Hartung, Christian G ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Density functional calculations; Hydroamination; Regioselectivity; Terminal alkynes; Titanocene

Indexed keywords

AMINES; AROMATIC COMPOUNDS; CATALYST ACTIVITY; CATALYST SELECTIVITY;

ALKYNES; HYDROAMINATION;

HYDROCARBONS;

ALKYNE DERIVATIVE; AMINE; ANILINE DERIVATIVE; BENZYLAMINE; BUTYLAMINE; CARBON; HYDRAZINE DERIVATIVE; HYDROGEN; PHENYL GROUP; SILICON DERIVATIVE; TITANIUM DERIVATIVE;

ADDITION REACTION; AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CORRELATION ANALYSIS; ELECTRICITY; HYDROGENATION; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; QUANTUM YIELD; REACTION ANALYSIS; STATISTICAL SIGNIFICANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 2942585374     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305674     Document Type: Article

References (157)

1. For general references, see: a) J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, pp. 768, and references therein; b) J. P. Collman, B. M. Trost, T. R. Veroeven, in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone), Pergamon Press, Oxford, 1982, pp. 892, and references therein; c) M. S. Gibson, in The Chemistry of Amino Group (Ed.: S. Patai), Wiley, New York, 1968, pp. 61.
2. For general references, see: a) J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, pp. 768, and references therein; b) J. P. Collman, B. M. Trost, T. R. Veroeven, in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone), Pergamon Press, Oxford, 1982, pp. 892, and references therein; c) M. S. Gibson, in The Chemistry of Amino Group (Ed.: S. Patai), Wiley, New York, 1968, pp. 61.
3. For general references, see: a) J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, pp. 768, and references therein; b) J. P. Collman, B. M. Trost, T. R. Veroeven, in Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone), Pergamon Press, Oxford, 1982, pp. 892, and references therein; c) M. S. Gibson, in The Chemistry of Amino Group (Ed.: S. Patai), Wiley, New York, 1968, pp. 61.
4. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
5. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
6. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
7. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
8. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
9. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
10. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
11. For leading reviews on hydroamination, see: a) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104; b) I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2003, 935; c) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579; d) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105; Angew. Chem. Int. Ed. 2001, 40, 3983; e) J.-J. Brunet, D. Neibecker, in Catalytic Heterofunctionalization, (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, p. 91; f) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675; g) J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235.
12. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
13. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
14. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
15. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
16. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
17. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
18. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
19. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
20. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
21. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
22. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
23. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
24. For alkalimetal and base catalyzed hydroamination, see: a) A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623; b) B. M. Trost, W. Tang, J. Am. Chem. Soc. 2003, 125, 8744; c) J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795; d) M. Beller, C. Breindl, Chemosphere 2001, 43, 21; e) C. G. Hartung, C. Breindl, A. Tillack, M. Beller, Tetrahedron 2000, 56, 5157; f) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. 1998, 110, 3571; Angew. Chem. Int. Ed. 1998, 37, 3389; g) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359; h) D. Steinborn, B. Dies, I. Wagner, R. Taube, Z. Chem. 1989, 29, 333; i) G. P. Pez, J. E. Galle, Pure Appl. Chem. 1985, 57, 1917; j) J. Wollensak, R. D. Closson, Org. Synth. 1963, 43, 45; k) R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124; l) B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
25. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
26. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
27. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
28. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
29. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
30. For acid-catalyzed hydroamination, see: a) M. Lequitte, F. Figueras, C. Moreau, S. Hub, J. Catal. 1996, 163, 255; b) A. Cermona, A. Corma, M. Iglesias, A. San José, F. Sánchez, J. Organomet. Chem. 1995, 492, 11; c) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Catal. 1994, 146, 249; d) N. Mizuno, M. Tabata, T. Uematsu, M. Iwamoto, J. Chem. Soc. Faraday Trans. 1 1993, 89, 3513; e) P. Fink, J. Datka, J. Chem. Soc. Faraday Trans. 1 1989, 85, 3079; f) M. Deeba, M. E. Ford, T. A. Johnson, J. Chem. Soc. Chem. Commun. 1987, 562.
31. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
32. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
33. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
34. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
35. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
36. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
37. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
38. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
39. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
40. For hydroamination mediated by early transition metals and lanthanoid complexes, see: a) D. V. Gribkov, K. C. Hultzsch, F. Hampel, Chem. Eur. J. 2003, 9, 4796; b) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560; c) P. N. O'Shaughnessy, P. Scott, Tetrahedron: Asymmetry 2003, 14, 1979; d) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161; e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886; f) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283; g) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797; Angew. Chem. Int. Ed. 2002, 41, 3645; h) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tetrahedron Lett. 2001, 42, 2933; i) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568; j) E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, 682; k) M. A. Giardell, V. P. Conticello, L. Brard, M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10241; l) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275; m) M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
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