An efficient and facile molecular iodine-promoted method for the synthesis of (E)-β-iodo vinylsulfones with high regio- and stereoselectivity using water as the solvent at room temperature is presented.

A useful and convenient method for C−H bond arylation of 8-aminoquinoline motifs on the remote C4 position was developed. This method shows good functional group tolerance toward various Grignard reagents and aminoquinoline via a nickel catalysis, giving the desired arylated products in good yields. The present method affords an efficient access to construct multisubstituted aminoquinolines.G iven the importance and versatility of quinoline derivatives as bioactive natural products, medicines, functional materials (Figure 1), 1 and directing groups for C− H functionalization in transition-metal-catalyzed reactions, 2 developing highly efficient and environmentally benign protocols for the synthesis of various functionalized quinolines is highly desired. In the past several decades, tremendous progress has been made for the construction of quinoline motifs via cyclization of anilines derivatives 3 or cyclization of substituted alkynes 4 intermolecularly or intramolecularly.However, the above-mentioned methods suffer from drawbacks such as high prefunctionalized starting materials and low selectivity in some cases. 4d An alternative synthetic method for functionalized quinolines is the site-selective modification of readily accessible quinoline frameworks via C−H functionalization. This method provides a quick access to functionalized quinolines. However, the regioselectivity has to be controlled. Many reactions for the C−H bond functionalization of the quinoline core are mainly on the position of C2, 5 C3, 6 C5, 7 and C8, 8 which are easily accessible. However, as for the functionalization of the important C4 position, 1d,e which is relatively less electrophilic (more nucleophilic) among the 8aminoquinioline core, progress is very slow. 9 In recent years, there are several reports concerning the functionalization on the C4 position of pyridine 10 or quinoline motif, 11 which provide some idea for the functionalization of 8-aminoquinoline. However, as for the remote C4−H functionalization of aminoquinolines, only three examples have been disclosed (Scheme 1). 9 In 2014, Zeng et al. reported the first two substrates of Fe-catalyzed remote C4−H allylation of 8aminoquinolines (Scheme 1a). 9a Wu et al. developed phosphonation of 8-aminoquinoline at C4 position via the combination of photocatalysis and transition metal catalysis

Herein, by dual C−O bond cleavage of cyclic ethers with Cu catalysis, we eventually led to the development of a selective three-component coupling of commercially available chemicals, carboxylic acids, ethers, and halogens to synthesize more than 70 iodoalkyl esters in the presence of TMSCF 3 . This allows for the concise synthesis of highly functionalized iodoalkyl esters directly. And the synthetic insect pheromones were also disclosed.