A novel class of potential herbicides, 3-indolylglycines, was synthesized using an effective, green and rapid approach via multicomponent reaction (aza-Friedel-Crafts) between indoles, aldehydes and anilines in a water/sodium dodecyl sulfate system. The main advantages of this methodology are ease of handling, scalable to gram scale and a metal-free approach. The reaction is compatible with a variety of functional groups, obtaining the desired products in moderate to excellent yields. The biological activity of the 3-indolylglycines was evaluated, and it was found that these compounds interfere with the germination and radicle growth of Lactuca sativa, mainly the compound 4k.

Apresentamos aqui nossos resultados da adição de tióis, catalisada por PhSeBr, a compostos carbonílicos α,β-insaturados sob condições brandas para obter regiosseletivamente β-mercapto cetonas ou tioacetais com altos rendimentos e seletividade. A reação foi principalmente controlada pela temperatura, na qual os produtos de adição 1,4 foram obtidos à temperatura de -20 ºC. Inversamente quando a reação foi realizada sob refluxo, tioacetais foram obtidos como único produto. O método admite diversos grupos funcionais, como alquilicos, benzilicos e arilicos com substituintes neutros, deficientes e ricos em elétrons no anel aromático.

We present herein results on the PhSeBr-catalyzed addition of thiols to α,β-unsaturated carbonyl compounds under mild conditions to afford regioselectivily β-mercapto ketones or thioacetals in high yields and selectivity. The reaction was highly controlled by the temperature in which, the 1,4-addition products were obtained when the temperature was -20 ºC, conversely when the reaction was carried out at reflux, the thioacetals were obtained as a sole product. The developed protocol stands a wide range of functional groups, in which alkyl, benzyl and aryl with neutral, electron deficient and electron rich substituents on the aromatic ring.

Neste trabalho desenvolvemos um método seletivo e eficiente para a síntese de derivados de 3-aril-2-(tiometil)-benzo[b]furanos, via reação de acoplamento com ácidos borônicos, catalisada por paládio. As condições reacionais usadas foram brandas e compatíveis com ácidos borônicos contendo substituintes retiradores, doadores de elétrons ou neutros.

A selective and efficient method for the synthesis of 3-aryl-2-(methylthio)benzo[b]furans derivatives by palladium catalyzed cross-coupling reaction with boronic acids has been developed. The reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron donating and neutral substituents.