메뉴 건너뛰기




Volumn 11, Issue 8, 2009, Pages 1733-1736

Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates

Author keywords

[No Author keywords available]

Indexed keywords

FEBUXOSTAT; HALOGENATED HYDROCARBON; MESYLIC ACID DERIVATIVE; NICKEL; THIAZOLE DERIVATIVE;

EID: 65249162972     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9001587     Document Type: Article
Times cited : (278)

References (108)
  • 5
    • 0036589259 scopus 로고    scopus 로고
    • A review on arvl-arvl bond formation: Hassan, J.; Sévignon, M.; Gozzi, C; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
    • A review on arvl-arvl bond formation: Hassan, J.; Sévignon, M.; Gozzi, C; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
  • 6
    • 0003397781 scopus 로고    scopus 로고
    • 2nd ed, de Meijere, A. Diederich, R, Eds, Wiley-VCH: Weinheim
    • Metal-Catahzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A. Diederich, R, Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Metal-Catahzed Cross-Coupling Reactions
  • 7
    • 33644905281 scopus 로고    scopus 로고
    • Reviews on C-H bond arylation of arenes: (a) Campeau, L.-C; Fagnou, K. Chem. Commun. 2006, 1253.
    • Reviews on C-H bond arylation of arenes: (a) Campeau, L.-C; Fagnou, K. Chem. Commun. 2006, 1253.
  • 14
    • 53949088904 scopus 로고    scopus 로고
    • Reviews on transition-metal-catalvzed C-C bond formation via C-H bond cleavage: (a) Kakiuchi, R; Kochi, T
    • Reviews on transition-metal-catalvzed C-C bond formation via C-H bond cleavage: (a) Kakiuchi, R; Kochi, T. Synthesis 2008, 3013.
    • (2008) Synthesis , pp. 3013
  • 21
    • 0001568295 scopus 로고    scopus 로고
    • Selected examples of Pd catalysis: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
    • Selected examples of Pd catalysis: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
  • 43
    • 0347296197 scopus 로고    scopus 로고
    • Selected examples of Rh catalysis: (a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
    • Selected examples of Rh catalysis: (a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
  • 49
    • 65249188609 scopus 로고    scopus 로고
    • References 6a and 6b
    • (g) References 6a and 6b.
  • 50
    • 34250844398 scopus 로고    scopus 로고
    • Angew. Chem., to
    • (h) Proch. S.; Kempe. R. Angew. Chem., to, Ed. 2007, 46, 3135.
    • (2007) Ed , vol.46 , pp. 3135
    • Proch, S.1    Kempe, R.2
  • 54
    • 0000592976 scopus 로고    scopus 로고
    • Selected examples of Ru catalysis: (a) Oi, S.; Fukita, S.; Hirata. N.; Watanuki, N.; Miyano, S.; Inoue, Y.Org. Lett. 2001, 3, 2579.
    • Selected examples of Ru catalysis: (a) Oi, S.; Fukita, S.; Hirata. N.; Watanuki, N.; Miyano, S.; Inoue, Y.Org. Lett. 2001, 3, 2579.
  • 63
    • 65249185414 scopus 로고    scopus 로고
    • Selected recent examples of other types of C-H bond arylation of arenes: (a) Kakiuchi. F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936.
    • Selected recent examples of other types of C-H bond arylation of arenes: (a) Kakiuchi. F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936.
  • 68
    • 38849126856 scopus 로고    scopus 로고
    • Li, B.-J.: Tian. S.-L.; Fang, Z.: Shi. Z.-L Angew. Chem., Int. Ed. 2008, 47, 1115.
    • (f) Li, B.-J.: Tian. S.-L.; Fang, Z.: Shi. Z.-L Angew. Chem., Int. Ed. 2008, 47, 1115.
  • 79
    • 33947091124 scopus 로고    scopus 로고
    • Selected examples of Ni-catalyzed cross-coupling using aryl electrophiles: (a) Tamao, K.; Sumitani. K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
    • Selected examples of Ni-catalyzed cross-coupling using aryl electrophiles: (a) Tamao, K.; Sumitani. K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
  • 82
    • 4544385923 scopus 로고    scopus 로고
    • Dankwardt. J. W. Angew. Chem., to Ed. 2004, 43, 2428.
    • (d) Dankwardt. J. W. Angew. Chem., to Ed. 2004, 43, 2428.
  • 86
    • 4544294920 scopus 로고    scopus 로고
    • Ni-catalyzed aromatic C-H bond functionalization: (a) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845.
    • Ni-catalyzed aromatic C-H bond functionalization: (a) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845.
  • 91
    • 65249186567 scopus 로고    scopus 로고
    • 20 was used without pretreatment, 3Aa was obtained in 23% yield.
    • 20 was used without pretreatment, 3Aa was obtained in 23% yield.
  • 92
    • 65249111431 scopus 로고    scopus 로고
    • dppe = 1,2-bis(diphenylphosphino)ethane; dppf = 1,1-bis(diphe- nylphosphino)ferrocene.
    • dppe = 1,2-bis(diphenylphosphino)ethane; dppf = 1,1-bis(diphe- nylphosphino)ferrocene.
  • 93
    • 65249186326 scopus 로고    scopus 로고
    • General Procedure. A 20-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar and Ni(OAc)2-4H 20 (10.6 mg, 0.05 mmol) was dried with a heatgun under vacuum and filled with argon after cooling to room temperature. To this vessel were added bipy or dppf (0.05 mmol, LiOf-Bu (60.0 mg, 0.75 mmol, heteroarene 1 (0.75 mmol, and haloarene 2 (0.50 mmol, followed by dry 1,4-dioxane (2.0 mL, The vessel was sealed with an O-ring tap and then heated (85-140 °C) in an eight-well reaction block with stirring. After cooling to room temperature, the mixture was passed through a short silica gel pad (EtOAc, The filtrate was concentrated, and the residue was subjected to preparative thin-layer chromatography (hexane/EtOAc) to afford a coupling product 3
    • 20 (10.6 mg, 0.05 mmol) was dried with a heatgun under vacuum and filled with argon after cooling to room temperature. To this vessel were added bipy or dppf (0.05 mmol), LiOf-Bu (60.0 mg, 0.75 mmol), heteroarene 1 (0.75 mmol), and haloarene 2 (0.50 mmol), followed by dry 1,4-dioxane (2.0 mL). The vessel was sealed with an O-ring tap and then heated (85-140 °C) in an eight-well reaction block with stirring. After cooling to room temperature, the mixture was passed through a short silica gel pad (EtOAc). The filtrate was concentrated, and the residue was subjected to preparative thin-layer chromatography (hexane/EtOAc) to afford a coupling product 3.
  • 94
    • 65249112016 scopus 로고    scopus 로고
    • 2/dppf is effective for aryl iodides/bromides at 140 °C.
    • 2/dppf is effective for aryl iodides/bromides at 140 °C.
  • 95
    • 65249147586 scopus 로고    scopus 로고
    • In entries 3-5, 3Aa (a phenyl group transfer product from dppf) was not observed.
    • In entries 3-5, 3Aa (a phenyl group transfer product from dppf) was not observed.
  • 96
    • 65249161528 scopus 로고    scopus 로고
    • Under current conditions, the following heteroarenes proved to be unreactive: 1-methylpyrrole, 1-phenylpyrazole, 3-methoxythiophene. A full scope of applicable (hetero)arenes will be reported in due course.
    • Under current conditions, the following heteroarenes proved to be unreactive: 1-methylpyrrole, 1-phenylpyrazole, 3-methoxythiophene. A full scope of applicable (hetero)arenes will be reported in due course.
  • 97
    • 0036643455 scopus 로고    scopus 로고
    • For successful/unsuccessful examples of organolithium cross- coupling, see: a
    • For successful/unsuccessful examples of organolithium cross- coupling, see: (a) Murahashi, S.-I. J. Orsanomet. Chem. 2002, 653, 27.
    • (2002) J. Orsanomet. Chem , vol.653 , pp. 27
    • Murahashi, S.-I.1
  • 104
    • 65249132842 scopus 로고
    • Synthesis: a, Jpn. Kokai Tokkyo Koho, 329647. Treatment study and mechanism
    • Synthesis: (a) Watanabe, K.; Tanaka, T.; Kondo, S. Jpn. Kokai Tokkyo Koho 1994, 329647. Treatment study and mechanism:
    • (1994)
    • Watanabe, K.1    Tanaka, T.2    Kondo, S.3
  • 107
    • 65249176668 scopus 로고    scopus 로고
    • Febuxostat has already been approved for use in Europe, and the FDA's Arthritis Advisory Committee has recently recommended approval for use in the U.S. If approved, febuxostat will be the first new treatment for the management of gout-associated hyperuricemia in more than 40 years.
    • Febuxostat has already been approved for use in Europe, and the FDA's Arthritis Advisory Committee has recently recommended approval for use in the U.S. If approved, febuxostat will be the first new treatment for the management of gout-associated hyperuricemia in more than 40 years.
  • 108
    • 65249165272 scopus 로고    scopus 로고
    • 2 ($610 for 2 g).
    • 2 ($610 for 2 g).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.