In the micelle of
PS-750-M, the presence of 3° amides from
the surfactant proline linker mimics dimethylformamide, dimethylacetamide,
and N-methyl-2-pyrrolidone. The resultant micellar
properties enable extremely fast amide couplings mediated by 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide
(without hydroxybenzotriazole), rather than expensive and specialized
coupling agents. Conditions have been developed wherein products precipitate,
and isolation by filtration completely avoids the use of organic solvent.
This methodology is scalable and avoids product epimerization.
A facile method to access (Z)-1,3-enynes is realized via sequential copper-catalyzed regio-and stereoselective borylation−protodeboronation of 1,3-diynes. Pinacolborane, copper(II) acetate, and Xantphos as the ligand efficiently install hydrogen and Bpin in a cis fashion, which is followed by rapid hydrolysis with water. The reaction has wide substrate scope and occurs in a chemoselective fashion.
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