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A Base‐Free Pd‐Precatalyst Mediated Suzuki‐Miyaura and Sonogashira Cross‐Coupling in Deep Eutectic Solvents
Author(s) -
Thiyagamurthy Pandurangan,
Khan Fazlur Rahman Nawaz
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000276
Subject(s) - sonogashira coupling , chemistry , deep eutectic solvent , catalysis , quinoline , potassium carbonate , ethylene glycol , coupling reaction , solvent , combinatorial chemistry , organic chemistry , medicinal chemistry , suzuki reaction , anhydrous , polymer chemistry , eutectic system , palladium , alloy
A volatile organic solvent‐free deep eutectic solvent (DES) was prepared by utilizing 1 : 10 ratio of potassium carbonate (PC) as a hydrogen bond acceptor (HBA) and ethylene glycol (EG) as a hydrogen bond donor (HBD). Subsequently, DES was utilized as a solvent in the Pd‐catalyzed Suzuki‐Miyaura or Sonogashira cross‐coupling reactions of boronic acids or acetylenes respectively with in situ generated 2‐bromobenzo[2,3][1,4]oxazepino[7,6‐b]quinoline, 3 The anhydrous conditions without air exclusion, low catalyst loading, low toxicity, high efficiency, low cost, and bioavailability are the advantages of DES in C−C bond forming reactions. Moreover, a gram‐scale reaction under mild conditions with an excellent yield was productive. The one‐pot reaction of 6‐bromo‐2‐chloroquinoline‐3‐carbaldehyde, 1 through 2‐bromobenzo [2,3][1,4]oxazepino [7,6‐b]quinoline, 3 intermediate, and subsequent Suzuki‐Miyaura or Sonogashira coupling was successfully attempted.