Abstract
We demonstrated a metal-free protocol for the construction of C–C bonds utilizing unprotected amino acids as radical sources.
Highlights
As an important building block, amino acids present the advantages of high stability, abundant natural resources, structural diversity and low cost, which make them ideal synthons for chemical synthesis.[1]
Synthetic utilization of a-aminoalkyl radicals generated by metal- or photo-catalyzed radical decarboxylation of N-protected amino acids has been achieved for the construction of C–C bonds (Scheme 1a and b)
The strategy for the generation of the alkyl radicals from unprotected amino acids was seldom applied to molecular transformations due to their tendency for rapid oxidation of unprotected a-aminoalkyl radicals
Summary
As an important building block, amino acids present the advantages of high stability, abundant natural resources, structural diversity and low cost, which make them ideal synthons for chemical synthesis.[1]. These reactions involved cross-coupling,[3] conjugate additions,[4] and Minisci reactions with electron-de cient heteroarenes.[5] the strategy for the generation of the alkyl radicals from unprotected amino acids was seldom applied to molecular transformations due to their tendency for rapid oxidation of unprotected a-aminoalkyl radicals. The resulting alkyl radicals via the multistep oxidative degradation of amino acids showed better selectivity and reactivity.[6] all of the reactions involving the use of amine acids as radical precursors reported so far require a toxic transition metal catalytic system.
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