Cross-coupling reactions of aryl pivalates with boronic acids

Journal of the American Chemical Society

Volumn 130, Issue 44, 2008, Pages 14422-14423

  Quasdorf, Kyle W ^a   Tian, Xia ^a   Garg, Neil K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; NICKEL; PHENOL DERIVATIVE;

ACYLATION; ARTICLE; CATALYST; CROSS COUPLING REACTION; ELECTRON TRANSPORT; OXIDATION; SUZUKI REACTION; TEMPERATURE;

EID: 55549084571     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806244b     Document Type: Article

References (27)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Meijere, A., Eds.; Wiley-VCH: Weinheim, 2004.
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3. (c) Top. Curr. Chem.; Miyaura, N., Ed.; Springer-Verlag: New York, 2002; Vol. 219.
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6. For a pertinent review, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
7. For aryl mesylate and tosylate cross-couplings, see: (a) Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049-3051.
8. (b) Tang, Z.; Hu, Q. J. Am. Chem. Soc. 2004, 126, 3058-3059.
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12. The Suzuki-Miyaura coupling of electron-deficient aryl methyl ethers was recently reported; see: Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866-4869.
13. Of the known methods for phenol coupling, the most common involves formation and reaction of the corresponding aryl triflates. However, these species are somewhat costly to prepare (see ref 7b), unable to serve as directing groups, and susceptible to base-promoted hydrolysis. Aryl mesylates and tosylates can also be utilized, although their utility does not yet appear to be general.
14. For unsuccessful attempts to effect the cross-coupling of O-acetylated phenols using Ni-catalysis, see: Guan, B.; Xiang, S.; Wu, T.; Sun, Z.; Wang, B.; Zhao, K.; Shi, Z. Chem. Commun. 2008, 1437-1439; see also ref 4.
15. Approximate reagent costs by Aldrich Chemical Co., Inc. are: (a) Trimethylacetyl chloride (pivaloyl chloride) = $10 per mol. (b) Triflic anhydride = $310 per mol. (c) Methanesulfonyl chloride = $10 per mol. (d) Iodomethane = $24 per mol.
16. For the insertion of Ni(O) into the acyl C-O bond of acylated phenols, see: Yamamoto, T.; Ishizu, J.; Kohara, T.; Komiya, S.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102, 3758-3764.
17. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
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19. (c) Doucet, H. Eur. J. Org. Chem. 2008, 2013-2030.
20. 8 transition metal, palladium, was completely ineffective at promoting the desired transformation under a variety of reaction conditions.
21. 3, dppe, dppf, and dppp provided trace amounts of cross-coupled products.
22. An excess of the arylboronic acid component is required because the trimeric boroxine, which comprises between 30 and 60% of commercially available arylboronic acids, is completely unreactive under these anhydrous conditions.
23. 2 is thought to undergo reduction to an active Ni(0) catalyst; see ref 3a.
24. 2, will soon be commercially available from Strem Chemicals Inc. (catalog #28-0091 ) or can be prepared in multigram quantities following a simple one-step protocol; see: (a) Stone, P. J.; Dori, Z. Inorg. Chim. Acta 1970, 5, 434-438.
25. (b) Barnett, K. W. J. Chem. Educ. 1974, 51, 422-423.
26. Arenes that possess an-OC(O)R substituent are known to undergo electrophilic aromatic substitution to afford orthol para substituted products; see: Smith, M. B.; March, J. March's Advanced Organic Chemistry, 6th ed.; John Wiley & Sons, Inc.: NJ, 2007; p 668.
27. The formation of ortho-brominated products was not observed, likely because of the steric bulk imposed by the pivalate group.