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Sterically demanding, sulfonated, triarylphosphines: Application to palladium-catalyzed cross-coupling, steric and electronic properties, and coordination chemistry

Tri(2,4-dimethyl-5-sulfonatophenyl)phosphine trisodium (TXPTS ¡¤Na3) and tri(4-methoxy-2-methyl5-sulfonatophenyl)phosphine trisodium (TMAPTS¡¤Na3) both provide more active catalysts for Suzuki and Sonogashira couplings of aryl bromides in aqueous solvents than tri(3-sulfonatophenyl)phosphine trisodium (TPPTS ¡¤Na3). In the Heck coupling, TXPTS ¡¤Na3 provides the most effective catalyst system. Cone angles determined from DFT-optimized structures show that both TXPTS¡¤Na3 (206) and TMAPTS¡¤Na3 (208) are significantly larger than TPPTS¡¤Na3 (165). The identity of the counterion had a significant effect on the calculated cone angles for these ligands. The electronic properties of these ligands determined by the CO stretching frequencies of trans-RhL2(Cl)CO complexes were identical, although calculated electronic parameters suggest subtle differences between these ligands. Similar to TPPTS¡¤Na3, both TXPTS¡¤Na3 and TMAPTS¡¤Na3 react with Pd(OAc)2 in aqueous solvents to give LnPd0 complexes and the corresponding phosphine oxide. The reduction of palladium(II) by TXPTS¡¤Na3 is significantly slower than is seen with TMAPTS¡¤Na3 or TPPTS¡¤Na3 at room temperature. Evidence of palladacycle complexes derived from TXPTS¡¤Na3 and TMAPTS¡¤Na3 by activation of an ortho-methyl substituent was also observed in ligand coordination studies and under catalytic reaction conditions.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method