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. 2009 Dec 16;131(49):17748-9.
doi: 10.1021/ja906477r.

Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates

Kyle W Quasdorf  1 , Michelle Riener, Krastina V Petrova, Neil K Garg
Affiliations

Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates

Kyle W Quasdorf et al. J Am Chem Soc. .

Abstract

The first Suzuki-Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise synthesis of the anti-inflammatory drug flurbiprofen.

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Figures

Figure 1
Figure 1
Approach to polysubstituted aromatics such as flurbiprofen.
Figure 2
Figure 2
Synthesis of flurbiprofen using orthogonal cross-couplings.
See this image and copyright information in PMC

References

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    1. The ortho-directing ability of methyl ethers is modest (see ref and refs therein), whereas ortho substitution of aryl pivalates presents a considerable challenge.

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