The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jun. 30, 2015

Filed:

May. 09, 2006
Applicants:

Stephen L. Buchwald, Newton, MA (US);

Artis Klapars, Edison, NJ (US);

Jon C. Antilla, Tampa, FL (US);

Gabriel E. Job, Ithaca, NY (US);

Martina Uhlenbrock, Berlin, DE;

Fuk Y. Kwong, Cambridge, MA (US);

Gero Nordmann, Boston, MA (US);

Edward J. Hennessy, Roslindale, MA (US);

Inventors:

Stephen L. Buchwald, Newton, MA (US);

Artis Klapars, Edison, NJ (US);

Jon C. Antilla, Tampa, FL (US);

Gabriel E. Job, Ithaca, NY (US);

Martina Uhlenbrock, Berlin, DE;

Fuk Y. Kwong, Cambridge, MA (US);

Gero Nordmann, Boston, MA (US);

Edward J. Hennessy, Roslindale, MA (US);

Assignee:
Attorneys:
Primary Examiner:
Int. Cl.
CPC ...
C07F 5/02 (2006.01); C07C 47/00 (2006.01); C07C 201/00 (2006.01); C07C 205/00 (2006.01); C07B 41/00 (2006.01); C07C 27/10 (2006.01); C07F 9/40 (2006.01); C07B 37/04 (2006.01); C07B 41/04 (2006.01); C07B 43/04 (2006.01); C07C 41/16 (2006.01); C07C 45/68 (2006.01); C07C 45/71 (2006.01); C07C 51/353 (2006.01); C07C 67/343 (2006.01); C07C 209/10 (2006.01); C07C 213/08 (2006.01); C07C 221/00 (2006.01); C07C 227/18 (2006.01); C07C 231/12 (2006.01); C07C 241/04 (2006.01); C07C 249/02 (2006.01); C07C 249/16 (2006.01); C07C 253/14 (2006.01); C07C 253/30 (2006.01); C07C 269/06 (2006.01); C07C 273/18 (2006.01); C07C 277/08 (2006.01); C07C 281/02 (2006.01); C07C 303/38 (2006.01); C07C 319/20 (2006.01); C07D 205/08 (2006.01); C07D 207/16 (2006.01); C07D 207/267 (2006.01); C07D 207/27 (2006.01); C07D 207/323 (2006.01); C07D 209/08 (2006.01); C07D 209/14 (2006.01); C07D 209/16 (2006.01); C07D 209/48 (2006.01); C07D 209/86 (2006.01); C07D 211/26 (2006.01); C07D 211/76 (2006.01); C07D 213/30 (2006.01); C07D 213/64 (2006.01); C07D 213/74 (2006.01); C07D 231/12 (2006.01); C07D 231/56 (2006.01); C07D 233/32 (2006.01); C07D 233/56 (2006.01); C07D 235/06 (2006.01); C07D 237/32 (2006.01); C07D 239/42 (2006.01); C07D 245/06 (2006.01); C07D 249/08 (2006.01); C07D 249/18 (2006.01); C07D 263/22 (2006.01); C07D 295/023 (2006.01); C07D 295/033 (2006.01); C07D 295/073 (2006.01); C07D 307/79 (2006.01); C07D 333/36 (2006.01); C07D 333/66 (2006.01); C07D 401/04 (2006.01); C07D 405/12 (2006.01); C07D 407/12 (2006.01); C07D 409/04 (2006.01); C07D 471/04 (2006.01); C07D 473/00 (2006.01); C07C 231/08 (2006.01);
U.S. Cl.
CPC ...
C07F 9/4056 (2013.01); C07B 37/04 (2013.01); C07B 41/04 (2013.01); C07B 43/04 (2013.01); C07C 41/16 (2013.01); C07C 45/68 (2013.01); C07C 45/71 (2013.01); C07C 51/353 (2013.01); C07C 67/343 (2013.01); C07C 209/10 (2013.01); C07C 213/08 (2013.01); C07C 221/00 (2013.01); C07C 227/18 (2013.01); C07C 231/12 (2013.01); C07C 241/04 (2013.01); C07C 249/02 (2013.01); C07C 249/16 (2013.01); C07C 253/14 (2013.01); C07C 253/30 (2013.01); C07C 269/06 (2013.01); C07C 273/1854 (2013.01); C07C 277/08 (2013.01); C07C 281/02 (2013.01); C07C 303/38 (2013.01); C07C 319/20 (2013.01); C07C 2101/14 (2013.01); C07D 205/08 (2013.01); C07D 207/16 (2013.01); C07D 207/267 (2013.01); C07D 207/27 (2013.01); C07D 207/323 (2013.01); C07D 209/08 (2013.01); C07D 209/14 (2013.01); C07D 209/16 (2013.01); C07D 209/48 (2013.01); C07D 209/86 (2013.01); C07D 211/26 (2013.01); C07D 211/76 (2013.01); C07D 213/30 (2013.01); C07D 213/64 (2013.01); C07D 213/74 (2013.01); C07D 231/12 (2013.01); C07D 231/56 (2013.01); C07D 233/32 (2013.01); C07D 233/56 (2013.01); C07D 235/06 (2013.01); C07D 237/32 (2013.01); C07D 239/42 (2013.01); C07D 245/06 (2013.01); C07D 249/08 (2013.01); C07D 249/18 (2013.01); C07D 263/22 (2013.01); C07D 295/023 (2013.01); C07D 295/033 (2013.01); C07D 295/073 (2013.01); C07D 307/79 (2013.01); C07D 333/36 (2013.01); C07D 333/66 (2013.01); C07D 401/04 (2013.01); C07D 405/12 (2013.01); C07D 407/12 (2013.01); C07D 409/04 (2013.01); C07D 471/04 (2013.01); C07D 473/00 (2013.01); C07C 2101/16 (2013.01); C07C 231/08 (2013.01); C07C 2101/08 (2013.01);
Abstract

The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods, such as the reaction of Z-X with C(L)(R)(R')in the present of a catalyst and a base, thereby forming C(Z)(R)(R′); wherein X represents I, Cl, alkylsulfonate, or arylsulfonate; Z represents optionally substituted aryl, heteroaryl or alkenyl; L represents H or a negative charge; catalyst comprises a copper atom or ion, and a ligand, wherein the ligand is an optionally substituted aryl alcohol, alkyl amine, 1,2-diamine, 1,2-aminoalcohol, 1,2-diol, imidazolium carbene, pyridine, or 1,10-phenanthroline; the ligand is a chelating ligand; and the base represents a Bronsted base; R represents H, optionally substituted alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl; R′ represents independently for each occurrence H, alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl, formyl, acyl, —COR″, —C(O)N(R), sulfonyl, —P(O)(OR″), —CN, or —NO; R″ represents independently for each occurrence optionally substituted alkyl, cycloalkyl, aralkyl, aryl, or heteroaryl; and C(R′)(R) taken together may represent nitrile.


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