Alcohols are ubiquitous motifs in pharmaceuticals and natural products. Therefore, site-selective functionalization of alcohols would allow for rapid access to a library of drug derivatives. However, the syntheses of site-selective functionalized products provide numerous synthetic challenges due to the inert sp<sup>3</sup> C-H bonds.  Herein, a strategy has been developed that allows for iterative ß,γ-functionalization of aliphatic alcohols.  This approach utilizes a radical chaperone to provide functionalization via a 1,5-hydrogen atom transfer, an <i>in-situ</i> desaturation, and a subsequent functionalization through iodonium formation and nucleophilic displacement to afford the amino-iodinated product.  This versatile amino-iodination allows access to a class of ß,γ-functionalization products, and provides an excellent synthetic intermediate to vast number of products.

Radical-chaperone mediated ß,γ-difunctionalization of alcohols

2019 Fall National Meeting

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