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US 9,850,261 B2Granted
Silicon-based cross coupling agents and methods of their use
AssigneeThe Trustees of the University of Pennsylvania
InventorsAdam T. Hoye, Won-Suk Kim, Dionicio Martinez-Solorio, Amos B. Smith, III, Rongbiao Tong, Minh Huu Nguyen, Luis Sanchez, Bruno Nicolas Melillo
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Abstract
Compositions and methods using silicon-based cross-coupling agents in the formation of carbon-carbon and carbon-nitrogen bonds are described.
Claims16
A method of cross-coupling a compound of formula NuLi with a compound of formula E-X to form a compound of formula Nu-E comprising contacting the compound of formula NuLi with the compound of formula E-X in the presence of a catalyst system consisting of palladium and a phosphate ligand, an ethereal solvent, and a compound of Formula I
- wherein
- Y is CH or N;
- R1 and R2 are independently C1-10 straight or branched-chain alkyl optionally substituted with one or more halogen, nitro, C1-6alkoxy, or aryl;
- R3 is H;
- aryl optionally substituted with one or more nitro, diC1-6alkylamino, C1-6alkoxy, or
- C1-6alkyl;
- heteroaryl optionally substituted with one or more nitro, diC16alkylamino,
- C1-6alkoxy, or C1-6alkyl;
- C1-10 straight or branched-chain alkyl optionally substituted with one or more halogen, nitro, C1-6alkoxy, or aryl;
- a polymer;
- or
- a resin support;
- R3a is H or C1-6alkyl optionally substituted with one or more halogen;
- and at least one R4, wherein each R4 is independently hydrogen, halogen, nitro,
- C1-6alkoxy, C1-6alkyl, aryl, or a resin support;
- for a time and under conditions sufficient to produce the compound of formula Nu-E;
- wherein
- Nu is an aryl compound, a heteroaryl compound, or an alkenyl compound;
- E is an aryl compound, a heteroaryl compound, or an alkenyl compound;
- and X is iodo, chloro, or bromo.
17 more elements
Dependencies are inferred from the claim text.