메뉴 건너뛰기




Volumn 15, Issue 29, 2009, Pages 7167-7179

The AZARYPHOS family of ligands for ambifunctional catalysis: Syntheses and use in ruthenium-catalyzed anti-markovnikov hydration of terminal alkynes

Author keywords

Alkynes; Catalysis; Phosphane ligands; Ruthenium; Synthetic methods

Indexed keywords

ALKYNES; LIGAND EFFECT; LONE PAIR; MARKOVNIKOV HYDRATION; METAL CENTERS; ORDERS OF MAGNITUDE; PHOSPHANE; PHOSPHANE LIGANDS; PHOSPHANES; PYRIDYL; SCALABLE SYNTHESIS; SYNTHETIC METHODS; SYNTHETIC STRATEGIES; TERMINAL ALKYNE;

EID: 67650607734     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900563     Document Type: Article
Times cited : (74)

References (105)
  • 12
    • 67650601466 scopus 로고    scopus 로고
    • E. Drent, EP0441446A1, 1991.
    • d) E. Drent, EP0441446A1, 1991.
  • 13
    • 67650572561 scopus 로고    scopus 로고
    • E. Drent, P. H. M. Budzelaar, W.W. Jager, EP0386833A1.
    • e)E. Drent, P. H. M. Budzelaar, W.W. Jager, EP0386833A1.
  • 14
    • 0035498330 scopus 로고    scopus 로고
    • f) G. Kiss, Chem. Rev. 2001, 101, 3435.
    • (2001) Chem. Rev , vol.101 , pp. 3435
    • Kiss, G.1
  • 30
    • 38349102530 scopus 로고    scopus 로고
    • For applications in cross-coupling, see: a
    • For applications in cross-coupling, see: a) S. Ishikawa, K. Manabe, Org. Lett. 2007, 9, 5593.
    • (2007) Org. Lett , vol.9 , pp. 5593
    • Ishikawa, S.1    Manabe, K.2
  • 34
    • 0141619221 scopus 로고    scopus 로고
    • While 6-substituted 2-pyridylphosphanes are usually synthesized by phosphination of the 2-halo precursors (see ref. [4a]). there is no single obvious synthetic route for the latter. For example, a recent paper on catalysis described syntheses of four 6-substituted 2-diphenylphosphinopyridines, in which each of the halogenated precursors was obtained by a different approach: L. P. Spencer, R. Altwer, P. Wei, L. Gelmini, J. Gauld, D. W Stephan, Organometallics 2003, 22, 3841.
    • While 6-substituted 2-pyridylphosphanes are usually synthesized by phosphination of the 2-halo precursors (see ref. [4a]). there is no single obvious synthetic route for the latter. For example, a recent paper on catalysis described syntheses of four 6-substituted 2-diphenylphosphinopyridines, in which each of the halogenated precursors was obtained by a different approach: L. P. Spencer, R. Altwer, P. Wei, L. Gelmini, J. Gauld, D. W Stephan, Organometallics 2003, 22, 3841.
  • 35
    • 67650614731 scopus 로고    scopus 로고
    • Based on the synthetic methods reported here, the compounds L8 (ALPYPHOS) and L15 (ARPYPHOS) have been prepared on a large scale and are currently on offer from the Aldrich chemical company.
    • Based on the synthetic methods reported here, the compounds L8 ("ALPYPHOS") and L15 ("ARPYPHOS") have been prepared on a large scale and are currently on offer from the Aldrich chemical company.
  • 36
    • 34247586308 scopus 로고    scopus 로고
    • Review on catalytic hydration of alkynes
    • Review on catalytic hydration of alkynes: L. Hintermann, A. Labonne, Synthesis 2007, 1121.
    • (2007) Synthesis , pp. 1121
    • Hintermann, L.1    Labonne, A.2
  • 37
    • 67650576465 scopus 로고    scopus 로고
    • Initial work on anti-Markovnikov hydration of terminal, alkynes: a M. Tokunaga, Y. Wakatsuki, Angew. Chem. 1998, 110, 3024;
    • Initial work on anti-Markovnikov hydration of terminal, alkynes: a) M. Tokunaga, Y. Wakatsuki, Angew. Chem. 1998, 110, 3024;
  • 47
    • 34547095484 scopus 로고    scopus 로고
    • A. Labonne, L. Zani, L. Hintermann, C. Bolm, J. Org. Chem. 2007, 72, 5704.
    • a) A. Labonne, L. Zani, L. Hintermann, C. Bolm, J. Org. Chem. 2007, 72, 5704.
  • 54
    • 67650588200 scopus 로고    scopus 로고
    • 2 fragment.
    • 2 fragment.
  • 57
    • 67650647988 scopus 로고    scopus 로고
    • 2 solution: M. A. Peterson, J. R. Mitchell, J. Org. Chem. 1997, 62, 8237.
    • 2 solution: M. A. Peterson, J. R. Mitchell, J. Org. Chem. 1997, 62, 8237.
  • 58
    • 0001629532 scopus 로고    scopus 로고
    • Catalytic amounts of CuI were added, which may not be necessary. For copper-mediated phosphinations, see
    • Catalytic amounts of CuI were added, which may not be necessary. For copper-mediated phosphinations, see: C. Meyer, H. Grützmacher, H. Pritzkow, Angew. Chem. 1997, 109, 2576;
    • (1997) Angew. Chem , vol.109 , pp. 2576
    • Meyer, C.1    Grützmacher, H.2    Pritzkow, H.3
  • 66
    • 67650647987 scopus 로고    scopus 로고
    • For this comparison, several X-ray crystal structures from the CSD database have been considered: ALATUC, PODWUA, WILJOQ, and WILPIQ
    • For this comparison, several X-ray crystal structures from the CSD database have been considered: ALATUC, PODWUA, WILJOQ, and WILPIQ.
  • 67
    • 67650638353 scopus 로고    scopus 로고
    • Diego State University, has informed us that this synthesis has been optimized in his group to give higher overall, yields. Nevertheless, the lengthy route and overall yield are still unsatisfactory. Personal communication by e-mail, 2006
    • Prof. D. B. Grotjahn, San. Diego State University, has informed us that this synthesis has been optimized in his group to give higher overall, yields. Nevertheless, the lengthy route and overall yield are still unsatisfactory. Personal communication by e-mail, 2006.
    • Prof1    Grotjahn, D.B.2    San3
  • 68
    • 67650594296 scopus 로고    scopus 로고
    • 3 in hot acetonitrile; see the Supporting Information.
    • 3 in hot acetonitrile; see the Supporting Information.
  • 70
    • 13644268558 scopus 로고    scopus 로고
    • Review on selectivity in. cross-coupling of heterocyclic substrates with multiple electrophilic sites
    • Review on selectivity in. cross-coupling of heterocyclic substrates with multiple electrophilic sites: S. Schröter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245.
    • (2005) Tetrahedron , vol.61 , pp. 2245
    • Schröter, S.1    Stock, C.2    Bach, T.3
  • 71
    • 11844277647 scopus 로고    scopus 로고
    • For monosubstitutions of dihalopyridines, see: a
    • For monosubstitutions of dihalopyridines, see: a) H. Ohmiya, H. Yorimitsu, K. Oshima, Chem. Lett. 2004, 33, 1240.
    • (2004) Chem. Lett , vol.33 , pp. 1240
    • Ohmiya, H.1    Yorimitsu, H.2    Oshima, K.3
  • 77
    • 67650620852 scopus 로고    scopus 로고
    • J. C. Loren, J. S. Siegel, Angew. Chem. 2001, 113, 776;
    • b) J. C. Loren, J. S. Siegel, Angew. Chem. 2001, 113, 776;
  • 87
    • 37349117351 scopus 로고    scopus 로고
    • IPr-HCl.=N,N'-bis(2,6-diisopropylphenyl)imidazolium chloride; this material was prepared according to our improved procedure: L. Hintermann, Beilstein J. Org. Chem. 2007, 3, 22.
    • IPr-HCl.=N,N'-bis(2,6-diisopropylphenyl)imidazolium chloride; this material was prepared according to our improved procedure: L. Hintermann, Beilstein J. Org. Chem. 2007, 3, 22.
  • 88
    • 67650614721 scopus 로고    scopus 로고
    • N-Heterocyclic Carben.es in Transition Metal Catalysis: Topics in Organometallic Chemistry, 21 (Ed.: F. Glorius), Springer, Heidelberg, 2007.
    • "N-Heterocyclic Carben.es in Transition Metal Catalysis": Topics in Organometallic Chemistry, Vol. 21 (Ed.: F. Glorius), Springer, Heidelberg, 2007.
  • 89
    • 67650601457 scopus 로고    scopus 로고
    • Incidentally, this appears to be the first reported case of a catalytic cross-coupling reaction of the 2,4,6-triphenylphenyl group
    • Incidentally, this appears to be the first reported case of a catalytic cross-coupling reaction of the 2,4,6-triphenylphenyl group.
  • 90
    • 0037182002 scopus 로고    scopus 로고
    • For use of thiophenol as a dummy group to desymmetrize 2, 6-dibromopyridine, see: V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, P Knochel, Tetrahedron 2002, 58, 4429.
    • For use of thiophenol as a "dummy" group to desymmetrize 2, 6-dibromopyridine, see: V. Bonnet, F. Mongin, F. Trécourt, G. Quéguiner, P Knochel, Tetrahedron 2002, 58, 4429.
  • 94
    • 0001021761 scopus 로고    scopus 로고
    • The direct conversion, of alkoxypyridines to halopyridines is fairly well documented for methoxy and a few other alkoxy groups: a M. Shiao, K. Tarng, Heterocycles 1990, 31, 637.
    • The direct conversion, of alkoxypyridines to halopyridines is fairly well documented for methoxy and a few other alkoxy groups: a) M. Shiao, K. Tarng, Heterocycles 1990, 31, 637.
  • 95
    • 0021123058 scopus 로고    scopus 로고
    • T. R. Kasturi, H. R. Y. Jois, L. Mathew, Synthesis 1984, 743.
    • b)T. R. Kasturi, H. R. Y. Jois, L. Mathew, Synthesis 1984, 743.
  • 101
    • 0029902679 scopus 로고    scopus 로고
    • DYNAFIT program
    • DYNAFIT program: P. Kuzmic, Anal. Biochem. 1996, 237, 260.
    • (1996) Anal. Biochem , vol.237 , pp. 260
    • Kuzmic, P.1
  • 102
    • 67650607520 scopus 로고    scopus 로고
    • Due to experimental errors, deviations of ±10% in RCA are not necessarily significant. However, the slightly higher activity induced by L8 over L7 has been reproduced in several independent experiments.
    • Due to experimental errors, deviations of ±10% in RCA are not necessarily significant. However, the slightly higher activity induced by L8 over L7 has been reproduced in several independent experiments.
  • 103
    • 67650617009 scopus 로고    scopus 로고
    • n values of pyridine (5.2), pyrimidine (1.3), and 1,3,5-triazine (<0): A. Albert, J. N. Phillips, J. Chem, Soc. 1956, 1294.
    • n values of pyridine (5.2), pyrimidine (1.3), and 1,3,5-triazine (<0): A. Albert, J. N. Phillips, J. Chem, Soc. 1956, 1294.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.