Theoretical study of reaction pathways for the rhodium phosphinecatalysed borylation of C-H bonds with pinacolborane

Dalton Transactions

Volumn , Issue 10, 2004, Pages 1556-1562

  Lam, Wai Han ^a   Lam, King Chung ^a   Lin, Zhenyang ^a   Shimada, Shigeru ^b,c   Perutz, Robin N ^d   Marder, Todd B ^c  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c DURHAM UNIVERSITY   (United Kingdom)

^d UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; BORON COMPOUNDS; CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; DISCRETE FOURIER TRANSFORMS; SINGLE CRYSTALS;

BOND ACTIVATION; LIGANDS; REGIOSELECTIVITY;

AROMATIC COMPOUNDS;

EID: 3042765623     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/B402632B     Document Type: Article

References (46)

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5. For transition metal promoted stoichiometric borylation of hydrocarbons, see: (a) K. M. Waltz and J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 11358; (b) K. M. Waltz, C. N. Muhoro and J. F. Hartwig, Organometallics, 1999, 18, 3383; (c) K. M. Waltz and J. F. Hartwig, Science, 1997, 277, 211; (d) for transition metal catalyzed borylation of hydrocarbons under photochemical conditions, see: H. Chen and J. F. Hartwig, Angew. Chem., Int. Ed., 1999, 38, 3391.
6. For transition metal promoted stoichiometric borylation of hydrocarbons, see: (a) K. M. Waltz and J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 11358; (b) K. M. Waltz, C. N. Muhoro and J. F. Hartwig, Organometallics, 1999, 18, 3383; (c) K. M. Waltz and J. F. Hartwig, Science, 1997, 277, 211; (d) for transition metal catalyzed borylation of hydrocarbons under photochemical conditions, see: H. Chen and J. F. Hartwig, Angew. Chem., Int. Ed., 1999, 38, 3391.
7. For transition metal promoted stoichiometric borylation of hydrocarbons, see: (a) K. M. Waltz and J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 11358; (b) K. M. Waltz, C. N. Muhoro and J. F. Hartwig, Organometallics, 1999, 18, 3383; (c) K. M. Waltz and J. F. Hartwig, Science, 1997, 277, 211; (d) for transition metal catalyzed borylation of hydrocarbons under photochemical conditions, see: H. Chen and J. F. Hartwig, Angew. Chem., Int. Ed., 1999, 38, 3391.
8. For transition metal promoted stoichiometric borylation of hydrocarbons, see: (a) K. M. Waltz and J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 11358; (b) K. M. Waltz, C. N. Muhoro and J. F. Hartwig, Organometallics, 1999, 18, 3383; (c) K. M. Waltz and J. F. Hartwig, Science, 1997, 277, 211; (d) for transition metal catalyzed borylation of hydrocarbons under photochemical conditions, see: H. Chen and J. F. Hartwig, Angew. Chem., Int. Ed., 1999, 38, 3391.
9. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
10. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
11. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
12. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
13. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
14. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
15. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
16. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
17. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
18. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
19. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
20. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
21. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
22. For transition metal catalyzed borylation of hydrocarbons under thermal conditions, see: (a) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2942; (b) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103; (c) R. E. Maleczka, F. Shi, D. Holmes and M. R. Smith III, J. Am. Chem. Soc., 2003, 125, 7792; (d) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Myaura, Tetrahedron Lett., 2002, 43, 5649; (e) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056; (f) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390; (g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr. and M. R. Smith III, Science, 2002, 295, 305; (h) M. K. Tse, J.-Y. Cho and M. R. Smith III, Org. Lett., 2001, 3, 2831; (i) J.-Y. Cho, C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 2000, 122, 12868; (j) H. Chen, S. Schlecht, T. C. Semple and J. F. Hartwig, Science, 2000, 287, 1995; (k) C. N. Iverson and M. R. Smith III, J. Am. Chem. Soc., 1999, 121, 7696; (l) for Pd/C catalysed borylation of hydrocarbons, see: T. Ishiyama, K. Ishida, J. Takagi and N. Miyaura, Chem. Lett., 2001, 1082; (m) for a review of metal catalyzed borylation of hydrocarbons, see: T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3; (n) for the borylation of vinyl-C-H bonds, which probably procedes by a rather different pathway, see, for example: R. B. Coapes, F. E. S. Souza, R. L1. Thomas, J. J. Hall and T. B. Marder, Chem. Commun., 2003, 614, and references therein.
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