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Please login or sign up for a free trial to access the full content. Method 2: Cross-Coupling Reactions

DOI: 10.1055/sos-SD-024-00952

Potapov, V. A.; Trofimov, B. A.Science of Synthesis, (200624989.

Cross-coupling reactions of (organosulfanyl)-, (organoselanyl)-, and (organotellanyl)ethenes with the formation of a new CC bond are well known.[‌32‌,‌226‌] The reactions with Grignard reagents are catalyzed by nickel complexes [e.g., NiCl2(dppp)].[‌226‌] More recently, the cross-coupling reaction of 1-(organosulfanyl)alk-1-ynes with boronic acids has been discovered.[‌227‌] This palladium-catalyzed, copper(I) carboxylate mediated reaction provides functionalized alkynes 81 in high yields (Scheme 34). The steroidal sulfide derivative 82 has been used in this reaction to give the 17α-[(4-methoxyphenyl)ethynyl]-substituted steroid 83 in 81% yield. This reaction uncovered new opportunities in the applications of 1-(organosulfanyl)alk-1-ynes in organic synthesis.

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