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π‐Allylpalladium Species in Micelles of FI‐750‐M for Sustainable and General Suzuki‐Miyaura Couplings of Unactivated Quinoline Systems in Water
Author(s) -
Handa Sachin,
Ibrahim Faisal,
Ansari Tharique N.,
Gallou Fabrice
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800958
Subject(s) - quinoline , micelle , chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , aqueous solution
General, clean, and sustainable Suzuki‐Miyaura cross‐couplings of 2‐and 4‐quinoline and isoquinoline systems have been demonstrated with use of π‐allyl Pd catalyst in the nanomicelles of environmentally benign, proline‐derived surfactant FI‐750‐M. Optimized reaction conditions mostly provided good‐to‐excellent yields up to gram‐scale with high selectivity and functional group tolerance. Control studies revealed the long‐term stability of the catalyst in FI‐750‐M. Both the catalyst and micellar reaction medium 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 that competitively inhibits reaction rate.