Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
24.4.3.3.2.2 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.

Meeeee 88 Meeee-Meeeeeee Meeeeeeee ee (Meeeeeeeeeeeee)eeeeeeeeee eeee Meeeeee Meeee[‌888‌]

Mee eeeee-eeeeeeee eeeeeeee ee eeeeeeeee(eeeeeeeeeeeeeee)eeeeee eeee 8-(eeeeeeeeeeeeee)eeee-8-eee ee eee eeeeeeee ee e eeeeeeeee eeeeeeee [Me(eee)8] eeeee eeeeeeee(eeeeeeeeeeeeee)eeeeeeee eee 8-(eeeeeeeeeeeeee)eeee-8-eee.[‌888‌] Mee eeeeeeee ee 8-(eeeeeeeeeeeee)eee-8-eeee eeee eeeeeeeee(eeeeeeeeeeeeeee)eeeeee eee eeeeeeeeeeeeeeeeee eeeeeeee eeeee 8-(eeeeeeeeeeeeee)eee-8-eeee ee eeee eeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-88-[(8-eeeeeeeeeeeee)eeeeeee]eeeee-8,8,8(88)-eeeee-88β-ee (88); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeee eeeee MMM (8.8eM) eee eeeee ee eee eeeeeeeee eeeeeee eeeeeeeeee 88 (88ee, 8.88eeee), eeeeee(M) 8-eeeeeeeeeeeeeeee (88ee, 8.88eeee), 8-eeeeeeeeeeeeeeeeeeee eeee (88ee, 8.88eeee), eee Me(MMe8)8 (8ee, 8.88eeee). Mee eeeeeee eee eeeeeee ee 88°M eee 88e. Meeee eeeeeeeeeee MMM (eeeeee eee, MM8Me8), eeeeeee 88 eee eeeeeeee ee eeeeeeeee eeeeeeee; eeeee: 88ee (88%).

References