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π-Allyl Palladium Species in Micelles of FI-750-M for Sustainable and General Suzuki-Miyaura Couplings of Quinoline Systems in Water

Gallou, Fabrice and Handa, Sachin (2018) π-Allyl Palladium Species in Micelles of FI-750-M for Sustainable and General Suzuki-Miyaura Couplings of Quinoline Systems in Water. ChemCatChem, 10 (19). pp. 4229-4233.

Abstract

General, clean, and sustainable Suzuki-Miyaura cross-couplings of quinoline and isoquinoline systems have been demonstrated with use of π-allyl Pd catalysts in environmentally benign proline-derived nanomicelles of FI-750-M. Optimized reaction conditions mostly provided good-to-excellent yields up to gram scale, with high selectivity and functional group tolerance. Control study revealed the long-term stability of catalyst in FI-750-M. Both the catalyst and nanomicelles have been recycled. The behavior of the nanomicelles has been elucidated with DLS and cryo-TEM measurements, and mechanistic investigations have revealed the reversible binding of quinoline nitrogen with palladium.

Item Type: Article
Date Deposited: 01 Jan 2019 00:45
Last Modified: 01 Jan 2019 00:45
URI: https://oak.novartis.com/id/eprint/36431

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