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Volumn 17, Issue 12, 2012, Pages 14573-14587

Stoichiometric and catalytic synthesis of alkynylphosphines

Author keywords

Homogeneous catalysis; Organophosphorus chemistry; Phosphine boranes; Phosphines

Indexed keywords

ALKYNE; BORANE DERIVATIVE; COPPER; PHOSPHINE DERIVATIVE; PHOSPHORUS; SILANE DERIVATIVE;

EID: 84871545856     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171214573     Document Type: Review
Times cited : (19)

References (34)
  • 3
    • 84871554873 scopus 로고    scopus 로고
    • Phosphine acetylenic macrocycles and cages: Synthesis and reactivity
    • 1st ed.; Peruzzini, M., Gonsalvi, L., Eds.; Springer: New York, NY, USA
    • Weymiens, W.; Slootweg, J.C.; Lammertsma, K. Phosphine Acetylenic Macrocycles and Cages: Synthesis and Reactivity. In Phosphorus Compounds Advanced Tools in Catalysis and Material Science, 1st ed.; Peruzzini, M., Gonsalvi, L., Eds.; Springer: New York, NY, USA, 2011; Volume 37, pp. 21-55.
    • (2011) Phosphorus Compounds Advanced Tools in Catalysis and Material Science , vol.37 , pp. 21-55
    • Weymiens, W.1    Slootweg, J.C.2    Lammertsma, K.3
  • 4
    • 77957159975 scopus 로고    scopus 로고
    • Construction of methylenecycloheptane frameworks through 7-exo-dig cyclisation of acetylenic silyl enol ethers catalyzed by triethynylphosphine- gold complex
    • Ito, H.; Ohmiya, H.; Sawamura, M. Construction of methylenecycloheptane frameworks through 7-exo-dig cyclisation of acetylenic silyl enol ethers catalyzed by triethynylphosphine-gold complex. Org. Lett. 2010, 12, 4380-4383.
    • (2010) Org. Lett. , vol.12 , pp. 4380-4383
    • Ito, H.1    Ohmiya, H.2    Sawamura, M.3
  • 5
    • 36549005121 scopus 로고    scopus 로고
    • Synthesis and enantioselectivity of P-chiral phosphine ligands with alkynyl groups
    • Imamoto, T.; Saitoh, Y.; Koide, A.; Ogura, T.; Yoshida, K. Synthesis and enantioselectivity of P-chiral phosphine ligands with alkynyl groups. Angew. Chem. Int. Ed. 2007, 46, 8636-8639.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8636-8639
    • Imamoto, T.1    Saitoh, Y.2    Koide, A.3    Ogura, T.4    Yoshida, K.5
  • 6
    • 77749296114 scopus 로고    scopus 로고
    • 1-Alkynylphosphines and their derivatives as key starting materials in creating new phosphines
    • Kondoh, A.; Yorimitsu, H.; Oshima, K. 1-Alkynylphosphines and their derivatives as key starting materials in creating new phosphines. Chem. Asian J. 2010, 5, 398-409.
    • (2010) Chem. Asian J. , vol.5 , pp. 398-409
    • Kondoh, A.1    Yorimitsu, H.2    Oshima, K.3
  • 9
    • 0000762523 scopus 로고
    • 3H-Phosphaallen-Alkinyl-1H-Phosphan-Tautomere
    • Märkl, G.; Reitinger, S. 3H-Phosphaallen-Alkinyl-1H-Phosphan- Tautomere. Tetrahedron Lett. 1988, 29, 463-466.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 463-466
    • Märkl, G.1    Reitinger, S.2
  • 10
    • 84982057242 scopus 로고
    • Chemistry of acetylenic ethers. LXII. Tertiary phosphines with an acetylene-phosphorus bond
    • Voskuil, W.; Arens, J.F. Chemistry of acetylenic ethers. LXII. Tertiary phosphines with an acetylene-phosphorus bond. Recl. Trav. Chim. Pays-Bas 1962, 81, 993-1008.
    • (1962) Recl. Trav. Chim. Pays-Bas , vol.81 , pp. 993-1008
    • Voskuil, W.1    Arens, J.F.2
  • 11
    • 0000652091 scopus 로고
    • Préparations propriétés chimiques et spectrographiques de phosphines α-acétyléniques
    • Charrier, C.; Chodkiewicz, W.; Cadiot, P. Préparations, propriétés chimiques et spectrographiques de phosphines α-acétyléniques. Bull. Soc. Chim. Fr. 1966, 1002-1011.
    • (1966) Bull. Soc. Chim. Fr. , pp. 1002-1011
    • Charrier, C.1    Chodkiewicz, W.2    Cadiot, P.3
  • 12
    • 79958783170 scopus 로고    scopus 로고
    • Synthesis of Z-alkenyl phosphorus compounds through hydroalumination and carbocupration of alkynyl precursors
    • Ortial, S.; Montchamp, J.-L. Synthesis of Z-alkenyl phosphorus compounds through hydroalumination and carbocupration of alkynyl precursors. Org. Lett. 2011, 13, 3134-3137.
    • (2011) Org. Lett. , vol.13 , pp. 3134-3137
    • Ortial, S.1    Montchamp, J.-L.2
  • 14
    • 84982336239 scopus 로고
    • Exchange reactions of some ethynyl-, diethynyl-, and butadiynyltin compounds
    • Hartmann, H. Exchange reactions of some ethynyl-, diethynyl-, and butadiynyltin compounds. Justus Liebigs Ann. Chem. 1968, 714, 1-7.
    • (1968) Justus Liebigs Ann. Chem. , vol.714 , pp. 1-7
    • Hartmann, H.1
  • 16
    • 0342617633 scopus 로고    scopus 로고
    • Preparation of polyfunctional phosphines using zinc organometallics
    • Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P. Preparation of polyfunctional phosphines using zinc organometallics. Tetrahedron: Asymmetry 1997, 8, 715-738.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 715-738
    • Langer, F.1    Püntener, K.2    Stürmer, R.3    Knochel, P.4
  • 17
    • 0034504189 scopus 로고    scopus 로고
    • Direct metalation of 1-alkynes using TiCl4/Et3N and the reactions of the organotitanium intermediates with electrophiles
    • Bharathi, P.; Periasamy, M. Direct metalation of 1-alkynes using TiCl4/Et3N and the reactions of the organotitanium intermediates with electrophiles. Organometallics 2000, 19, 5511-5513.
    • (2000) Organometallics , vol.19 , pp. 5511-5513
    • Bharathi, P.1    Periasamy, M.2
  • 18
    • 3643102447 scopus 로고
    • Chemistry of acetylenic titanium compounds
    • Krause, N.; Seebach, D. Chemistry of acetylenic titanium compounds. Chem. Ber. 1987, 120, 1845-1851.
    • (1987) Chem. Ber. , vol.120 , pp. 1845-1851
    • Krause, N.1    Seebach, D.2
  • 19
    • 0345603481 scopus 로고    scopus 로고
    • New approach to phosphinoalkynes based on Pd-and Ni-catalyzed cross-coupling of terminal alkynes with chlorophosphanes
    • Beletskaya, I.P.; Afanasiev, V.V.; Kazankova, M.A.; Efimova, I.V. New approach to phosphinoalkynes based on Pd-and Ni-catalyzed cross-coupling of terminal alkynes with chlorophosphanes. Org. Lett. 2003, 5, 4309-4311.
    • (2003) Org. Lett. , vol.5 , pp. 4309-4311
    • Beletskaya, I.P.1    Afanasiev, V.V.2    Kazankova, M.A.3    Efimova, I.V.4
  • 20
    • 34247138826 scopus 로고    scopus 로고
    • Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes
    • Kondoh, A.; Yorimitsu, H.; Oshima, K. Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes. J. Am. Chem. Soc. 2007, 129, 4099-4104.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 4099-4104
    • Kondoh, A.1    Yorimitsu, H.2    Oshima, K.3
  • 21
    • 0347949737 scopus 로고    scopus 로고
    • A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes
    • Afanasiev, V.V.; Beletskaya, I.P.; Kazankova, M.A.; Efimova, I.V.; Antipin, M.U. A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes. Synthesis 2003, 2835-2838.
    • (2003) Synthesis , pp. 2835-2838
    • Afanasiev, V.V.1    Beletskaya, I.P.2    Kazankova, M.A.3    Efimova, I.V.4    Antipin, M.U.5
  • 22
    • 33845959705 scopus 로고    scopus 로고
    • Using triethynylphosphine ligands bearing bulky end caps to create a holey catalytic environment: Application to gold (I)-catalyzed alkyne cyclizations
    • Ochida, A.; Ito, H.; Sawamura, M. Using triethynylphosphine ligands bearing bulky end caps to create a holey catalytic environment: Application to gold(I)-catalyzed alkyne cyclizations. J. Am. Chem. Soc. 2006, 128, 16486-16487.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 16486-16487
    • Ochida, A.1    Ito, H.2    Sawamura, M.3
  • 23
    • 34250852369 scopus 로고    scopus 로고
    • Phosphorus ligands with a large cavity: Synthesis of triethynylphosphines with bulky end caps and application to the rhodium-catalyzed hydrosilylation of ketones
    • Ochida, A.; Sawamura, M. Phosphorus ligands with a large cavity: Synthesis of triethynylphosphines with bulky end caps and application to the rhodium-catalyzed hydrosilylation of ketones. Chem. Asian J. 2007, 2, 609-618.
    • (2007) Chem. Asian J. , vol.2 , pp. 609-618
    • Ochida, A.1    Sawamura, M.2
  • 24
    • 79952849188 scopus 로고    scopus 로고
    • Copper-catalyzed synthesis of alkynylphosphine derivatives: Unprecedented use of nucleophilic phosphorus compounds
    • Bernoud, E.; Alayrac, C.; Delacroix, O.; Gaumont, A.-C. Copper-catalyzed synthesis of alkynylphosphine derivatives: Unprecedented use of nucleophilic phosphorus compounds. Chem. Commun. 2011, 47, 3239-3241.
    • (2011) Chem. Commun. , vol.47 , pp. 3239-3241
    • Bernoud, E.1    Alayrac, C.2    Delacroix, O.3    Gaumont, A.-C.4
  • 25
    • 84859138321 scopus 로고    scopus 로고
    • Neutral copper-phosphido-borane complexes: Synthesis, characterization, and use as precatalysts in Csp-P bond formation
    • Abdellah, I.; Bernoud, E.; Lohier, J.-F.; Alayrac, C.; Toupet, L.; Lepetit, C.; Gaumont, A.-C. Neutral copper-phosphido-borane complexes: Synthesis, characterization, and use as precatalysts in Csp-P bond formation. Chem. Commun. 2012, 48, 4088-4090.
    • (2012) Chem. Commun. , vol.48 , pp. 4088-4090
    • Abdellah, I.1    Bernoud, E.2    Lohier, J.-F.3    Alayrac, C.4    Toupet, L.5    Lepetit, C.6    Gaumont, A.-C.7
  • 26
    • 0034075208 scopus 로고    scopus 로고
    • Synthesis of functionalized mono-, di-, tri-and tetraphosphines: Attempted application to prepare hyperbranched polymers and dendrimers built with phosphines at each branching point
    • Huc, V.; Balueva, A.; Sebastian, R.-M.; Caminade, A.-M.; Majoral, J.-P. Synthesis of functionalized mono-, di-, tri-and tetraphosphines: Attempted application to prepare hyperbranched polymers and dendrimers built with phosphines at each branching point. Synthesis 2000, 726-730.
    • (2000) Synthesis , pp. 726-730
    • Huc, V.1    Balueva, A.2    Sebastian, R.-M.3    Caminade, A.-M.4    Majoral, J.-P.5
  • 27
    • 33847800667 scopus 로고
    • Asymmetric hydrogenation with a complex of rhodium and a chiral bisphosphine
    • Knowles, W.S.; Sabacky, M.J.; Vineyard, B.D.; Weinkauff, D.J. Asymmetric hydrogenation with a complex of rhodium and a chiral bisphosphine. J. Am. Chem. Soc. 1975, 97, 2567-2568.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2567-2568
    • Knowles, W.S.1    Sabacky, M.J.2    Vineyard, B.D.3    Weinkauff, D.J.4
  • 28
    • 24644493747 scopus 로고    scopus 로고
    • Preparation and X-ray analysis of novel carbonyltungsten (0) complexes of diphosphinidenecyclobutenes
    • Yoshifuji, M.; Ichikawa, Y.; Yamada, N.; Toyota, K. Preparation and X-ray analysis of novel carbonyltungsten(0) complexes of diphosphinidenecyclobutenes. Chem. Commun. 1998, 27-28.
    • (1998) Chem. Commun. , pp. 27-28
    • Yoshifuji, M.1    Ichikawa, Y.2    Yamada, N.3    Toyota, K.4
  • 30
    • 0035038879 scopus 로고    scopus 로고
    • Selective reductions in the sphere of organophosphorus compounds
    • Keglevich, G.; Gaumont, A.-C.; Denis, J.-M. Selective reductions in the sphere of organophosphorus compounds. Heteroat. Chem. 2001, 12, 161-167.
    • (2001) Heteroat. Chem. , vol.12 , pp. 161-167
    • Keglevich, G.1    Gaumont, A.-C.2    Denis, J.-M.3
  • 31
    • 0001496937 scopus 로고
    • Primary alkynylphosphines and allenylphosphines
    • Guillemin, J.-C.; Savignac, P.; Denis, J.-M. Primary alkynylphosphines and allenylphosphines. Inorg. Chem. 1991, 30, 2170-2173.
    • (1991) Inorg. Chem. , vol.30 , pp. 2170-2173
    • Guillemin, J.-C.1    Savignac, P.2    Denis, J.-M.3
  • 33
    • 34250339792 scopus 로고
    • Reduction of phosphine oxides, a mild and practical synthesis of secondary P-ethynylphosphines
    • Pilard, J.-F.; Baba, G.; Gaumont, A.-C.; Denis, J.-M. Reduction of phosphine oxides, a mild and practical synthesis of secondary P-ethynylphosphines. Synlett 1995, 1168-1170.
    • (1995) Synlett , pp. 1168-1170
    • Pilard, J.-F.1    Baba, G.2    Gaumont, A.-C.3    Denis, J.-M.4
  • 34
    • 67650528785 scopus 로고    scopus 로고
    • Copper-catalyzed aerobic oxidative coupling of terminal alkynes with H-phosphonates leading to alkynylphosphonates
    • Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. Copper-catalyzed aerobic oxidative coupling of terminal alkynes with H-phosphonates leading to alkynylphosphonates. J. Am. Chem. Soc. 2009, 131, 7956-7957.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7956-7957
    • Gao, Y.1    Wang, G.2    Chen, L.3    Xu, P.4    Zhao, Y.5    Zhou, Y.6    Han, L.-B.7


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