Negishi Coupling
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The Negishi Coupling is the nickel or palladium-catalyzed stereoselective reaction of organozincs and organic halides. • Reaction mechanism: • 1. Initially, the electron-rich Pd(0) catalyst inserts into the R–X bond of the organic halide. This oxidative addition forms an organo-Pd(II)-complex. • 2. Subsequent transmetalation with the organozinc reagent forms a hetero-organometallic complex. • 3. Before the next step, isomerization is necessary to bring the organic ligands next to each other into cis positions. • 4. Finally, reductive elimination leads to the formation of a C–C bond and releases the cross-coupled product while regenerating the Pd(0) catalyst. • Pinterest: • https://www.pinterest.es/pin/67166973... • References: • NROChemistry: https://nrochemistry.com/negishi-coup... • Example #1. Yifan Deng, Chia-Ping H. Yang, and Amos B. Smith III, J. Am. Chem. Soc. 2021, 143, 4, 1740–1744. https://pubs.acs.org/doi/pdf/10.1021/... • Example #2. D. Ma, Y. Liu, Z. Wang, Angew. Chem. Int. Ed. 2017, 56, 7886. https://onlinelibrary.wiley.com/doi/1...
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