Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air

The Suzuki–Miyaura cross-coupling reaction plays a fundamental role in modern synthetic organic chemistry, both in academia and industry. For this reason, scientists continue to search for new, more effective, cheaper and environmentally friendly procedures. Recently, micellar synthetic chemistry ha...

Full description

Bibliographic Details
Main Authors: Dawod Yousif, Silvia Tombolato, Elmehdi Ould Maina, Riccardo Po, Paolo Biagini, Antonio Papagni, Luca Vaghi
Format: Article
Language:English
Published: MDPI AG 2021-12-01
Series:Organics
Subjects:
Online Access:https://www.mdpi.com/2673-401X/2/4/25
Description
Summary:The Suzuki–Miyaura cross-coupling reaction plays a fundamental role in modern synthetic organic chemistry, both in academia and industry. For this reason, scientists continue to search for new, more effective, cheaper and environmentally friendly procedures. Recently, micellar synthetic chemistry has been demonstrated to be an excellent strategy for achieving chemical transformations in a more efficient way, thanks to the creation of nanoreactors in aqueous environments using selected surfactants. In particular, the cheap and commercially available surfactant Kolliphor EL (a polyethoxylated castor oil derivative) has been used with success to achieve metal-catalyzed transformations in water with high yields and short reaction times, with the advantage of using air-sensitive catalysts without the need for inert atmosphere. In this work, the Kolliphor EL methodology was applied to the Suzuki cross-coupling reaction between thiophene and aniline, using the highly effective catalyst Pd(dtbpf)Cl<sub>2</sub>. The cross-coupling products were achieved at up to 98% yield, with reaction times of up to only 15 min, working at room temperature and without the need for inert atmosphere.
ISSN:2673-401X