Hypervalent Iodine Reagents Enable C–H Alkynylation with Iminophenylacetic Acids via Alkoxyl Radicals
Organic Letters(2022)
Abstract
Here we report δ-C–H alkynylation to synthesize various δ-alkynols from iminophenylacetic acids. The hypervalent iodine-coordinated benziodoxole-alkoxyl-iminophenylacetic acid complex was the key intermediate and was characterized by X-ray crystallography for the first time. δ-C–H alkynylation is compatible with sensitive functional groups, including azides, aldehydes, and free alcohols, for the synthesis of δ-alkynols with diversified substituents in excellent regioselectivity. This reaction extends to δ-hydroxylalkene and δ-hydroxylnitrile synthesis, and the δ-alkynol products are easily derivatized to other valuable bifunctional building blocks.
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Key words
Hypervalent Iodine Compounds,C–H Functionalization,C–H Activation,Directed C–H Functionalization
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