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CAS indexed 478 chemical substances from this document.
CAS subject entries for this document include: Amines, preparation; Ethers, preparation; Ketones, preparation; and 16 additional concepts. | |
CAPLUS COPYRIGHT 2005 ACS on STN
| TITLE:
| Biaryl phosphine and amine ligands for improved transition metal-catalyzed processes |
| INVENTOR(S):
| Buchwald, Stephen; Old, David W.; Wolfe, John P.; Palucki, Michael; Kamikawa, Ken; Chieffi, Andrew; Sadighi, Joseph P.; Singer, Robert A.; Ahman, Jens |
| PATENT ASSIGNEE(S):
| Massachusetts Institute of Technology, USA |
| SOURCE:
| PCT Int. Appl., 397 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- -------------------- --------
WO 2000002887 A2 20000120 WO 1999-US15450 19990709
WO 2000002887 A3 20000629
W: CA, JP
RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL,
PT, SE
US 6395916 B1 20020528 US 1998-113478 19980710
US 6307087 B1 20011023 US 1999-231315 19990113
US 6867310 B1 20050315 US 1999-239024 19990127
CA 2336691 AA 20000120 CA 1999-2336691 19990709
EP 1097158 A2 20010509 EP 1999-933785 19990709
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT,
IE, FI
JP 2002520328 T2 20020709 JP 2000-559117 19990709
ABSTRACT:
The present invention relates to the prepn. of novel biaryl phosphine and amine ligands (I) [wherein A and B = independently fused monocyclic or polycyclic cycloalkyl, cycloalkenyl, aryl, or heterocyclic rings of 4-8 atoms; X = NR2, PR2, AsR2, OR, or SR; Y = NR2, PR2, AsR2, OR, SR, SiR3, alkyl, or H; R-R6 = independently H, halogen, (hetero)alkyl, alkenyl, alkynyl, hydroxy, alkoxy, silyloxy, amino, nitro, sulfhydryl, amide, carbonyl, ketone, anhydride, silyl, thioalkyl, ketone, ester, nitrile, (hetero)aryl, etc.] for transition metals and their use in metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. Unexpected improvements over the prior art were demonstrated in transition metal-catalyzed aryl amination reactions, Suzuki couplings giving both biaryl and alkylaryl products, arylations and vinylations at the position .alpha. to carbonyl groups, and carbon-oxygen bond formation. The ligands and methods of the invention enable transformations utilizing aryl chlorides and bromides at room temp. at synthetically useful rates with extremely small amts. of catalyst relative to the limiting reagent. For example, coupling of p-chlorobenzonitrile and morpholine was catalyzed by 2.5 mol% Pd2(dba)3, 7.5 mol% of 2-(N,N-dimethylamino)-2'-(dicyclohexylphosphino)biphenyl, and NaOBu-t in DME at room temp. to provide 4-(4-morpholinyl)benzonitrile in 96% yield. Thus, the subject processes provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.
Updated 5/10/2007 1:03:15 PM
