Coupling Heck-Sonogashira

Cross-coupling reactions (Sonogashira or Heck reactions) of 1-bromo-l-fluor-oalkenes, which are generally prepared through the reaction of an aldehyde with CFBra and PPha. ... 

Keywords Homogeneous catalysis Cross-coupling Microwave Heck Sonogashira Buchwald-Hartwig... 

Keywords Cross-coupling Heck Microwave Protease inhibitors Sonogashira... 

In the last quarter-century, the practice and art of organic synthesis has been revolutionized by the discovery of transition metal catalyzed organic transformations, at a rate that would make the discoverer of islands in the St. Lawrence Seaway envious [78]. Aside from the demonstrated DoM-Ar-Ar cross-coupling connection above and the initial promise of acy-lative, 200 — 201 (Scheme 49) [79] and carbonylative, 202 —> 203 —> 204 or Suzuki-Miyaura, 203 — 205 (Scheme 50) [80] coupling, the establishment of potential DoM links to the literature-visible, already reliable, but not yet mature Heck, Sonogashira, and Grubbs metatheses will undoubtedly reap benefits for synthetic aromatic and heteroaromatic chemistry. 

The synthesis commenced with a site-selective Heck-Sonogashira coupling of the easily prepared indole 174 and known alkyne 175. Selective reduction of the resulting alkyne 176 to the corresponding cis olefin followed by a two-step... 

Thus, the Castro (63JOC3313) and the Heck-Sonogashira cross-couplings (75TL4467 91COS521) are very attractive methods for obtaining the different alkynylpyrazoles. 

Furthermore, a number step growth metal-catalyzed C—C combining reactions like Stille, Kumada, or Suzuki coupling, Heck and Sonogashira-Hagihara reactions, a.o., are employed especially for the preparation of highly aromatic and conjugated polymers (see Fig. 3.21). 

They explored this strategy for the synthesis of chartelline C (145) and it was started by taking indole 156 and alkyne 157, which after Heck-Sonogashira coupling yielded compound 158 (Scheme 14) [74],... 

A. Datta, K. Ebert, H. Plenio, Nanofiltration for homogeneous catalysis separation Soluble polymer-supported palladium catalysts for Heck, Sonogashira, and Suzuki coupling of aryl halides, OrganometaUics 22 (2003) 4685-4691. 

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