Back to results
US 7,223,879 B2Granted
Ligands for metals and improved metal-catalyzed processes based thereon
AssigneeMassachusetts Institute of Technology
InventorsStephen L. Buchwald, Xiaohua Huang, Danilo Zim
Life of this patent
Estimating the term…
Abstract
One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.
Claims24
A ligand represented by structure I:
- wherein
- R is selected independently for each occurrence from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, and —(CH2)m—R80;
- the A and A′ rings of the biphenyl core independently may be unsubstituted or substituted with R1 and R2, respectively, any number of times up to the limitations imposed by stability and the rules of valence;
- R1 and R2, when present, are selected independently for each occurrence from the group consisting of ethyl, propyl, butyl, pentyl, hexyl, cycloalkyl, heterocycloalkyl, heteroaryl, aralkyl, heteroaralkyl, —Si(R)3, and —(CH2)m—R80;
- R80 represents an unsubstituted or substituted aryl, a cycloalkyl, a cycloalkenyl, a heterocycle, or a polycycle;
- m is independently for each occurrence an integer in the range 0 to 8 inclusive;
- and
- the ligand, when chiral, is a mixture of enantiomers or a single enantiomer.
5 more elements
A ligand represented by structure II:
- wherein
- R is selected independently for each occurrence from the group consisting of cycloalkyl, and —(CH2)m—R80;
- R′ is selected independently for each occurrence from the group consisting of alkyl, cycloalkyl, and —(CH2)m—R80;
- the A and A′ rings of the biphenyl core independently may be unsubstituted or substituted with R1 and R2, respectively, any number of times up to the limitations imposed by stability and the rules of valence;
- R1 and R2, when present, are selected independently for each occurrence from the group consisting of alkyl, cycloalkyl, halogen, —Si(R)3, and —(CH2)m—R80;
- R80 represents independently for each occurrence cycloalkyl or aryl;
- m is independently for each occurrence an integer in the range 0 to 8 inclusive;
- and
- the ligand, when chiral, is a mixture of enantiomers or a single enantiomer.
6 more elements
A ligand represented by structure III:
- wherein
- R′ is selected independently for each occurrence from the group consisting of alkyl, cycloalkyl, and —(CH2)m—R80;
- the A and A′ rings of the biphenyl core independently may be unsubstituted or substituted with R1 and R2, respectively, any number of times up to the limitations imposed by stability and the rules of valence;
- R1 and R2, when present, are selected independently for each occurrence from the group consisting of alkyl, cycloalkyl, halogen, —Si(R)3, and —(CH2)m—R80;
- R80 represents independently for each occurrence cycloalkyl or aryl;
- m is independently for each occurrence an integer in the range 0 to 8 inclusive;
- and
- the ligand, when chiral, is a mixture of enantiomers or a single enantiomer.
5 more elements
Dependencies are inferred from the claim text.