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Volumn 17, Issue 47, 2011, Pages 13230-13239

Aryl-aryl bond formation by the fluoride-free cross-coupling of aryldisiloxanes with aryl bromides

Author keywords

biaryls; C C coupling; cross coupling; silicon; synthetic methods

Indexed keywords

ARYL BROMIDES; BIARYLS; BOND FORMATION; C-C COUPLING; COST-EFFICIENT; CROSS-COUPLINGS; DIFFERENT SUBSTRATES; NOVEL STRATEGIES; OPTIMISATIONS; REACTION CONDITIONS; STRUCTURAL MOTIFS; SYNTHETIC METHODS;

EID: 81255166928     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102285     Document Type: Article
Times cited : (11)

References (66)
  • 20
    • 12344293447 scopus 로고    scopus 로고
    • and references therein
    • For a useful discussion of the variety of organosilanes used in biaryl synthesis and the disadvantages of fluoride activation, see:, S. E. Denmark, M. H. Ober, Adv. Synth. Catal. 2004, 346, 1703, and references therein. The authors also report a fluoride-free, base-activated coupling protocol using aryl(dimethyl)silanols.
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1703
    • Denmark, S.E.1    Ober, M.H.2
  • 21
    • 0025283733 scopus 로고
    • For examples of organosilane species that have been successfully employed as aryl donors in fluoride-activated cross-coupling reactions with aryl halides see: for aryl(fluro)silanes: Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1990, 31, 2719
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2719
    • Hatanaka, Y.1    Hiyama, T.2
  • 25
    • 0000831654 scopus 로고    scopus 로고
    • aryl (trialkoxy)silanes
    • See ref. 19(c); aryl(halo)silacyclobutanes: S. E. Denmark, Z. C. Wu, Org. Lett. 1999, 1, 1495; aryl (trialkoxy)silanes
    • (1999) Org. Lett. , vol.1 , pp. 1495
    • Denmark, S.E.1    Wu, Z.C.2
  • 29
    • 15044357725 scopus 로고    scopus 로고
    • aryl(triallyl)silanes
    • M. L. Clarke, Adv. Synth. Catal. 2005, 347, 303; aryl(triallyl)silanes
    • (2005) Adv. Synth. Catal. , vol.347 , pp. 303
    • Clarke, M.L.1
  • 55
    • 33749651001 scopus 로고    scopus 로고
    • A notable exception are the aryl(2-(hydroxymethyl)phenyl)dimethylsilanes developed by Hiyama and co-workers, which could be successfully reacted with a broad range of aryl iodides in the presence of potassium carbonate and copper iodide to furnish biaryl derivatives without the need for fluoride activators. See: Y. Nakao, A. K. Sahoo, A. Yada, J. S. Chen, T. Hiyama, Sci. Technol. Adv. Mater. 2006, 7, 536
    • (2006) Sci. Technol. Adv. Mater. , vol.7 , pp. 536
    • Nakao, Y.1    Sahoo, A.K.2    Yada, A.3    Chen, J.S.4    Hiyama, T.5
  • 58
    • 33644543025 scopus 로고    scopus 로고
    • Y. Nakao, A. K. Sahoo, H. Imanaka, A. Yada, T. Hiyama, Pure Appl. Chem. 2006, 78, 435. However, the use of aryl bromides in such reactions is much less common; the development of a protocol that allows the coupling of a wide range of aryl bromides under mild fluoride-free conditions with a masked silanol(ate)would be of value as bromo derivatives are more readily available and typically easier to synthesise than their iodo counterparts
    • (2006) Pure Appl. Chem. , vol.78 , pp. 435
    • Nakao, Y.1    Sahoo, A.K.2    Imanaka, H.3    Yada, A.4    Hiyama, T.5
  • 62
    • 33344460691 scopus 로고    scopus 로고
    • In a DoE, the ranges of the factors to be investigated (defining the covered experimental space) should be sufficiently wide so as to ensure that the optimum is residing within the experimental space studied, but not so large that experiments become impractical (e.g., an extremely long reaction time) or indeed, that the overall process yields optimised values for a given reaction component that are undesirable (e.g., a very large catalyst loading). See Ref. [50].: V. K. Aggarwal, A. C. Staubitz, M. Owen, Org. Process Res. Dev. 2006, 10, 64.
    • (2006) Org. Process Res. Dev. , vol.10 , pp. 64
    • Aggarwal, V.K.1    Staubitz, A.C.2    Owen, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.