A Practical Synthesis of Biaryls via a Thermal Decarboxylative Pd-Catalyzed Cross-Coupling Reaction Operating at Moderate Temperature

Typeset version

 

TY  - JOUR
  - Mitchell, D,Coppert, DM,Moynihan, HA,Lorenz, KT,Kissane, M,McNamara, OA,Maguire, AR
  - 2011
  - January
  - Organic Process Research ; Development
  - A Practical Synthesis of Biaryls via a Thermal Decarboxylative Pd-Catalyzed Cross-Coupling Reaction Operating at Moderate Temperature
  - Validated
  - ()
  - ARENECARBOXYLIC ACIDS AROMATIC CARBOXYLATES ARYL HALIDES SALTS
  - 15
  - 981
  - 985
  - The palladium-catalyzed decarboxylative cross-coupling of aminothiophene carboxylate and 1-bromo-4-chlorobenzene to produce 3-amino-2-(4-chlorophenyl)thiophene (2) is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and TBAB. Through use of a mixed-solvent system of DMF and NMP, it was possible to operate the cross-coupling system at 80 degrees C. An assessment of carbon dioxide liberation, which provides insight into the reaction operating parameters, is also discussed.
  - DOI 10.1021/op200030t
DA  - 2011/01
ER  - 
@article{V108666792,
   = {Mitchell,  D and Coppert,  DM and Moynihan,  HA and Lorenz,  KT and Kissane,  M and McNamara,  OA and Maguire,  AR },
   = {2011},
   = {January},
   = {Organic Process Research ; Development},
   = {A Practical Synthesis of Biaryls via a Thermal Decarboxylative Pd-Catalyzed Cross-Coupling Reaction Operating at Moderate Temperature},
   = {Validated},
   = {()},
   = {ARENECARBOXYLIC ACIDS AROMATIC CARBOXYLATES ARYL HALIDES SALTS},
   = {15},
  pages = {981--985},
   = {{The palladium-catalyzed decarboxylative cross-coupling of aminothiophene carboxylate and 1-bromo-4-chlorobenzene to produce 3-amino-2-(4-chlorophenyl)thiophene (2) is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and TBAB. Through use of a mixed-solvent system of DMF and NMP, it was possible to operate the cross-coupling system at 80 degrees C. An assessment of carbon dioxide liberation, which provides insight into the reaction operating parameters, is also discussed.}},
   = {DOI 10.1021/op200030t},
  source = {IRIS}
}
AUTHORSMitchell, D,Coppert, DM,Moynihan, HA,Lorenz, KT,Kissane, M,McNamara, OA,Maguire, AR
YEAR2011
MONTHJanuary
JOURNAL_CODEOrganic Process Research ; Development
TITLEA Practical Synthesis of Biaryls via a Thermal Decarboxylative Pd-Catalyzed Cross-Coupling Reaction Operating at Moderate Temperature
STATUSValidated
TIMES_CITED()
SEARCH_KEYWORDARENECARBOXYLIC ACIDS AROMATIC CARBOXYLATES ARYL HALIDES SALTS
VOLUME15
ISSUE
START_PAGE981
END_PAGE985
ABSTRACTThe palladium-catalyzed decarboxylative cross-coupling of aminothiophene carboxylate and 1-bromo-4-chlorobenzene to produce 3-amino-2-(4-chlorophenyl)thiophene (2) is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and TBAB. Through use of a mixed-solvent system of DMF and NMP, it was possible to operate the cross-coupling system at 80 degrees C. An assessment of carbon dioxide liberation, which provides insight into the reaction operating parameters, is also discussed.
PUBLISHER_LOCATION
ISBN_ISSN
EDITION
URL
DOI_LINKDOI 10.1021/op200030t
FUNDING_BODY
GRANT_DETAILS