Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle

Balaram S Takale; Ruchita R Thakore; Gianluca Casotti; Xaiohan Li; Fabrice Gallou; Bruce H Lipshutz

doi:10.1002/anie.202014141

Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle

Angew Chem Int Ed Engl. 2021 Feb 19;60(8):4158-4163. doi: 10.1002/anie.202014141. Epub 2021 Jan 21.

Authors

Balaram S Takale¹, Ruchita R Thakore¹, Gianluca Casotti^{1

2}, Xaiohan Li¹, Fabrice Gallou³, Bruce H Lipshutz¹

Affiliations

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, 93106, USA.
² Dipartimento di Chimica e Chimica Industriale, Universitá di Pisa, Via G. Moruzzi 13, 56124, Pisa, Italy.
³ CHAD, Novartis Pharma AG, 4056, Basel, Switzerland.

PMID: 33180988
DOI: 10.1002/anie.202014141

Abstract

An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500-1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.

Keywords: Stille couplings; cross-coupling; green chemistry; nanostructures; palladium.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't