The carbonylative Suzuki–Miyaura reaction between aryl tosylates/triflates with arylboronic acid is herein reported, using base-free conditions and a balloon pressure of carbon monoxide.
A series of cinchona alkaloid derivatives were used to catalyze the asymmetric anti-Mannich-type reaction of 3-methyl-2-oxindole with N-tosyl aryl aldimines. The resulting anti-3,3-disubstituted 2-oxindole products were obtained in good yields (up to 92%) with high diastereo- and enantioselectivities (anti/syn up to 97:3 and 91% ee).
An efficient procedure for the synthesis of biaryls was catalyzed by Pd(CH 3 CN) 4 (BF 4 ) 2 is reported. This Pd-catalyzed cross-coupling reaction of aryltrifluoroborates with sodium arenesulfinates was developed under mild and environmentally benign conditions, in water without any ligand or additive. The reaction gave a range of structurally diverse unsymmetrical bi-aryl molecules with excellent yields, in which the byproduct was sulfur dioxide. It is worth noting that this protocol is also applicable to many heterocyclic aromatics such as thiophene, furan, pyridine, quinoline, isoquinoline and indole.
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