PMID- 33905170
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20210628
LR  - 20231107
IS  - 1864-564X (Electronic)
IS  - 1864-5631 (Print)
IS  - 1864-5631 (Linking)
VI  - 14
IP  - 12
DP  - 2021 Jun 21
TI  - Palladium Catalyst Recycling for Heck-Cassar-Sonogashira Cross-Coupling Reactions 
      in Green Solvent/Base Blend.
PG  - 2591-2600
LID - 10.1002/cssc.202100623 [doi]
AB  - The identification of a green, versatile, user-friendly, and efficient 
      methodology is necessary to facilitate the use of Heck-Cassar-Sonogashira (HCS) 
      cross-coupling reaction in drug discovery and industrial production in the 
      pharmaceutical segment. The Heck-Cassar and Sonogashira protocols, using 
      N-hydroxyethylpyrrolidone (HEP)/water/N,N,N',N'-tetramethyl guanidine (TMG) as 
      green solvent/base mixture and sulfonated phosphine ligands, allowed to recycle 
      the catalyst, always guaranteeing high yields and fast conversion under mild 
      conditions, with aryl iodides, bromides, and triflates. No catalyst leakage or 
      metal contamination of the final product were observed during the HCS recycling. 
      To our knowledge, a turnover number (TON) up to 2375, a turnover frequency (TOF) 
      of 158 h(-1) , and a process mass intensity (PMI) around 7 that decreased around 
      3 after solvent, base, and palladium recovery, represent one of the best results 
      to date using a sustainable protocol. The Heck-Cassar protocol using sSPhos was 
      successfully applied to the telescoped synthesis of Erlotinib (TON: 1380; TOF: 
      46 h(-1) ).
CI  - (c) 2021 The Authors. ChemSusChem published by Wiley-VCH GmbH.
FAU - Fantoni, Tommaso
AU  - Fantoni T
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Bernardoni, Sara
AU  - Bernardoni S
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Mattellone, Alexia
AU  - Mattellone A
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Martelli, Giulia
AU  - Martelli G
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Ferrazzano, Lucia
AU  - Ferrazzano L
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Cantelmi, Paolo
AU  - Cantelmi P
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Corbisiero, Dario
AU  - Corbisiero D
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Tolomelli, Alessandra
AU  - Tolomelli A
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Cabri, Walter
AU  - Cabri W
AD  - Department of Chemistry Giacomo Ciamician Alma Mater Studiorum, University of 
      Bologna, Via Selmi 2, 40136, Bologna, Italy.
FAU - Vacondio, Federica
AU  - Vacondio F
AD  - Department of Food and Drug Sciences, University of Parma, Parco Area delle 
      Scienze 27/a, 43124-, Parma, Italy.
FAU - Ferlenghi, Francesca
AU  - Ferlenghi F
AD  - Department of Food and Drug Sciences, University of Parma, Parco Area delle 
      Scienze 27/a, 43124-, Parma, Italy.
FAU - Mor, Marco
AU  - Mor M
AD  - Department of Food and Drug Sciences, University of Parma, Parco Area delle 
      Scienze 27/a, 43124-, Parma, Italy.
FAU - Ricci, Antonio
AU  - Ricci A
AD  - Innovation and Development, Fresenius kabi iPsum, via San Leonardo 23, 45010, 
      Villadose (RO), Italy.
LA  - eng
GR  - Faggi Enrico S.p.A./
GR  - Alma Mater Studiorum University of Bologna/
GR  - Fresenius kabi/
GR  - FKOL, Gurgaon India/
PT  - Journal Article
DEP - 20210511
PL  - Germany
TA  - ChemSusChem
JT  - ChemSusChem
JID - 101319536
SB  - IM
PMC - PMC8251985
OTO - NOTNLM
OT  - Heck-Cassar-Sonogashira
OT  - TPPTS
OT  - cross-coupling
OT  - green chemistry
OT  - homogeneous catalysis
COIS- The authors declare no conflict of interest.
EDAT- 2021/04/28 06:00
MHDA- 2021/04/28 06:01
PMCR- 2021/07/02
CRDT- 2021/04/27 12:26
PHST- 2021/04/22 00:00 [revised]
PHST- 2021/03/25 00:00 [received]
PHST- 2021/04/28 06:00 [pubmed]
PHST- 2021/04/28 06:01 [medline]
PHST- 2021/04/27 12:26 [entrez]
PHST- 2021/07/02 00:00 [pmc-release]
AID - CSSC202100623 [pii]
AID - 10.1002/cssc.202100623 [doi]
PST - ppublish
SO  - ChemSusChem. 2021 Jun 21;14(12):2591-2600. doi: 10.1002/cssc.202100623. Epub 2021 
      May 11.