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. 2010 Sep 29;132(38):13194-6.
doi: 10.1021/ja1066459.

Direct C-H arylation of electron-deficient heterocycles with arylboronic acids

Ian B Seiple  1 , Shun Su, Rodrigo A Rodriguez, Ryan Gianatassio, Yuta Fujiwara, Adam L Sobel, Phil S Baran
Affiliations

Direct C-H arylation of electron-deficient heterocycles with arylboronic acids

Ian B Seiple et al. J Am Chem Soc. .

Abstract

A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

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Figures

Figure 1
Figure 1
(A) Overview of the addition of arylboronic acids to electron-deficient heterocycles. (B) Initial findings with respect to arylboronic acid reactivity.
Figure 2
Figure 2
A mechanism consistent with previous studies by Minisci.
Scheme 1
Scheme 1
Direct arylation of quinine.a a Quinine (0.125 mmol), arylboronic acid (0.25 + 0.125 mmol), TFA (0.375 mmol), AgNO3 (0.025 mmol), K2S2O8 (0.25 mmol), 23 °C, 3–24 h; isolated yield of chromatographically and spectroscopically pure product displayed.
See this image and copyright information in PMC

References

    1. Suzuki A, Brown HC. Organic Synthesis Via Boranes. Volume 3. Milwaukee, WI: Aldrich; 2003.

    1. For selected reviews on the Minisci reaction, see: Minisci F, Vismara E, Fontana F. Heterocycles. 1989;28:489. Minisci F, Fontana F, Vismara E. J. Heterocycl. Chem. 1990;27:79. Harrowven DC, Sutton BJ. Prog. Heterocycl. Chem. 2004;16:27.

    1. Minisci F, Vismara V, Fontana F, Morini G, Serravalle M, Giordano C. J. Org. Chem. 1986;51:4411.
    1. Seiple IB, Su S, Young IS, Lewis CA, Yamaguchi J, Baran PS. Angew. Chem. Int. Ed. 2010;49:1095. - PMC - PubMed

    1. For general reviews, see: Boulton AJ, McKillop A. In: Comprehensive Heterocyclic Chemistry. Katrizky AR, Rees CW, editors. Vol. 2. New York: Pergamon; 1984. pp. 262–270. Joule JA, Mills K. Heterocyclic Chemistry, Fourth Edition. Malden, MA: Blackwell; 2000. For a recent example with potassium t-Butoxide, suggested to be proceeding through a radical mechanism, see: Yanagisawa S, Ueda K, Tanaguchi T, Itami K. Org. Lett. 2008;10:4673.

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