Herein, we present m-C–H olefination on
derivatives of phenylacetic acids by tethering with a simple nitrile-based
template through palladium catalysis. Notably, the versatility of
the method is evaluated with a wide range of phenylacetic acid derivatives
for obtaining the meta-olefination products in fair
to excellent yields with outstanding selectivities under mild conditions.
Significantly, the present strategy is successfully exemplified for
the synthesis of drugs/natural product analogues (naproxen, ibuprofen,
paracetamol, and cholesterol).
This article describes the development of a new aliphatic nitrile-template-directed remote meta-selective C−H olefin functionalization reaction of arenes. Remarkably, unlike the previous reports, this process is feasible at room temperature and enabled the formation of products with excellent regioselectivity. The present protocol encompasses a broad spectrum of substituted dihydrocinnamic acids and olefins, producing meta-C−H olefinated products (up to 96% yield). In addition, the efficacy of the present method has been showcased by the synthesis of various drug analogues (e.g., cholesterol, estrone, ibuprofen, and naproxen). Significantly, the robustness of meta-olefination was also demonstrated by gram-scale synthesis. The new nitrile-based meta-directing template, in particular, could be easily synthesized in two steps and recycled under mild conditions.
We have developed nickel-catalyzed synthesis of 3-aryl benzofurans from ortho-alkenyl phenols via intramolecular dehydrogenative coupling. O2 gas served as an oxidant and 3-aryl benzofurans were synthesized in good to very good yields.
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