Substitutive Approach Toward Heteroaromatic Amino Alcohols Accessed Through Dioxolanyl Radical Linchpin

Aryl ethanolamines are an important functional group found in a variety of pharmaceuticals and natural products. For the past century, the main strategies for synthesizing these compounds are through Henry reactions followed by reductions or olefin oxidations using aldehyde or styrene starting materials. Herein, we disclose a highly adaptable synthesis of heteroaromatic amino alcohols enabled by a dioxolanyl radical linchpin strategy to take advantage of highly abundant aryl bromides and complex amine precursors. This methodology has been demonstrated across a variety of substrates, including a diverse set of thirteen distinct heteroarene classes. After mild deprotection, these diols can be simply activated and functionalized for chemoselective amino alcohol formation. The chosen retrosynthetic disconnection allows the incorporation of commercially available amines directly in synthesis.