Transition-metal-catalyzed carbon-nitrogen bond-forming methods using carbene ligands
AssigneeMassachusetts Institute of Technology
InventorsStephen L. Buchwald, Joseph M. Fox
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Abstract
The present invention relates to a process for the preparation of N-aryl amine and N-aryl amide compounds. Generally, the process of the present invention involves reacting a compound having a primary or secondary amino or amido group with an arylating compound, in the presence of a weak base and a transition metal catalyst, under reaction conditions effective to form an N-aryl amine or N-aryl amide compound, the transition metal catalyst comprising a Group 8 metal, e.g., Ni, Pd, or Pt, and at least one carbene-containing ligand. Typically, the transition metal catalyst is formed in a preceding step from the conjugate acid form of the carbene ligand, a stoichiometric amount of a strong base, and a Group 8 metal atom or ion.
Claims20
A method represented by Scheme 1:
- wherein
- X represents I, Br, Cl, alkylsulfonate, or arylsulfonate;
- Ar represents optionally substituted aryl or heteroaryl;
- catalyst consists essentially of a Group 8 atom or ion;
- and at least one carbene-containing ligand;
- base represents a phosphate, carbonate, bicarbonate, fluoride, tertiary amine, or hydride;
- R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl, heteroaryl, formyl, acyl, —CO2alkyl, —CO2aryl, —CO2aralkyl, —N(R′)acyl, —N(R′)C(O)Oalkyl, —N(R′)C(O)Oaryl, —N(R′)C(O)Oaralkyl, —N═C(alkyl)2, or —N═C(aryl)2;
- R′ represents H, alkyl, cycloalkyl, aralkyl, aryl, heteroaryl, formyl, acyl, or amino;
- R and R′ taken together may represent C(alkyl)2, or =C(aryl)2;
- and
- R and R′ are optionally connected by a covalent bond to form a cyclic structure which incorporates the amine nitrogen.
Dependencies are inferred from the claim text.