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Abstract
Herein, we report a visible-light-mediated synthesis of highly complex 1,6-amino alcohols through the 1,2-carboimination of alkenes leading by an energy transfer (EnT) mechanism. This protocol successfully achieved the simultaneous formation of C(sp3)–C(sp3) and C(sp3)–N bonds after several cascade steps: homolysis of the O-N bond, carbon dioxide and acetonitrile extrusion, 1,5-hydrogen atom transfer (HAT), Giese-type and radical additions. This additive and metal-free method presented a broad functional tolerance, and its value was proved with the late-stage installation of the 1,6-amino alcohol motif in biomolecules and pharmaceuticals. Finally, the versatility of the 1,6-iminyl alcohols products is showcased through their conversion to a variety of useful intermediates applicable to target-directed synthesis.
Supplementary materials
Title
Supplementary Material of the Visible-Light-Assisted the Metal-Free 1,2-Carboimination of Alkenes to Synthesize Complex 1,6-Amino Alcohols
Description
Experimental procedures and analytical data (1H, 13C and 19F NMR, MS, and melting points) can be found in the ESI. Copies of NMR spectra are also provided.
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