ethyl 4-(2-biphenylyl)-2-butenoate

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• Chemical Name: ethyl 4-(2-biphenylyl)-2-butenoate
• CAS No.: 90401-65-3
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34

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Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides

10.1021/ol049827e

The study presents a copper sulfate-pentahydrate (CuSO?·5H?O) and 1,10-phenanthroline catalyzed cross-coupling protocol for synthesizing ynamides from alkynyl bromides and amides. This method is more environmentally friendly than using CuCN or copper halides and allows for the synthesis of various ynamides, including sulfonyl and heteroaromatic amine substituted ones. The researchers optimized the protocol by screening different Cu(I) and Cu(II) salts, ligands, solvents, concentrations, bases, and temperatures. They found that CuSO?·5H?O with 1,10-phenanthroline as the ligand provided the best results, yielding ynamides in good isolated yields and suppressing homocouplings. The protocol was successfully applied to a range of substrates, including previously poor ones like azacamphor, imidazolidinone, and acyclic urethanes, as well as lactams. It was also effective in preparing sulfonyl ynamides and vinylogous ynamides with various heteroaromatic amines, demonstrating its versatility and potential impact on organic synthesis.

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