Shang-Dong Yang

Direct Annulations toward Phosphorylated Oxindoles: Silver‐Catalyzed Carbon‐Phosphorus Functionalization of Alkenes

the NSFC (Nos. 21272100);Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT: IRT1138);Research Fund for the Doctoral Program of Higher Education of China (Nos. 20100211120014)

Metal-free carbonitration of alkenes using K2S2O8

A novel metal-free oxidative carbonitration of alkenes by a nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct valuable nitro-containing oxindoles.

A Mild, Selective Copper-Catalyzed Oxidative Phosphonation of α-Amino Ketones

A novel and selective method of simple copper-salt catalyzed phosphonation of α-amino carbonyl compounds to afford imidoylphosphonates is reported. This reaction system has a broad reaction scope. The convenient and environmentally benign process makes this protocol very attractive.

Pd(II)-Catalyzed Ph2(O)P-Directed C–H Olefination toward Phosphine–Alkene Ligands

The Pd(II)-catalyzed Ph2(O)P-directed C-H olefination to synthesize alkene-phosphine compounds is reported. In contrast to previous examples of various directing groups that guide selective C-H activation, the Ph2(O)P group not only acts as the directing group but also serves to construct the alkene-phosphine ligands. The monoprotected amino acid (MPAA) ligand Ac-Leu-OH is found to promote this reaction in a significant manner.

Palladium-Catalyzed sp2 and sp3 C–H Bond Activation and Addition to Isatin toward 3-Hydroxy-2-oxindoles

The first Pd(II)-catalyzed C-H addition to isatins by direct sp(2)/sp(3) C-H bond activation for the construction of 3-substituted-3-hydroxy-2-oxindoles is reported. The bidentate nitrogen ligands were found to promote this reaction. Specifically, the preliminary bioassay indicated that 3-(5-chlorobenzoxazole)-3-hydroxy-N-benzyl-2-oxindole (2w) is a new inhibitor of human kidney cancer and hepatocellular carcinoma cells. Moreover, this reaction system exhibits great functional group tolerance and requires no directing group, extra base, or additives.

P(O)R2 directed Pd(II)-catalyzed C(sp2)–H acylation

A novel method for the Pd(II)-catalyzed C–H acylation of 2-phosphorylbiphenyl with α-oxocarboxylic acids, aldehydes, alcohols and toluene is described. This reaction provides efficient access to various substituted 2′-phosphorylbiphenyl-2-acyl compounds.

P(O)R2-directed Pd-catalyzed C–H functionalization of biaryl derivatives to synthesize chiral phosphorous ligands

Summary Chiral phosphorus ligands have been widely used in transition metal-catalyzed asymmetric reactions. Herein, we report a new synthesis approach of chiral biaryls containing a phosphorus moiety using P(O)R2-directed Pd-catalyzed C–H activation; the functionalized products are produced with good enantioselectivity.

Catalyst-free three-component reaction to synthesize chiral α-amino phosphine oxides

A three-component reaction for high diastereoselective synthesis of chiral α-amino phosphine oxides has been developed and displayed environmentally friendly and atom efficient characteristics. The reaction proceeds smoothly without catalysts or additives.