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CAS indexed 80 chemical substances from this document.
CAS subject entries for this document include: Coupling reaction catalysts; Coupling reaction; Aryl halides; and 13 additional concepts. | |
CAPLUS COPYRIGHT 2006 ACS on STN
| TITLE:
| Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions |
| INVENTOR(S):
| Buchwald, Stephen L.; Anderson, Kevin W. |
| PATENT ASSIGNEE(S):
| Massachusetts Institute of Technology, USA |
| SOURCE:
| PCT Int. Appl., 94 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- -------------------- --------
WO 2006074315 A2 20060713 WO 2006-US365 20060109
WO 2006074315 A3 20060831
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH,
CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD,
GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR,
KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX,
MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE,
SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC,
VN, YU, ZA, ZM, ZW
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE,
IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ,
CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,
GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY,
KG, KZ, MD, RU, TJ, TM
US 2006173186 A1 20060803 US 2006-328426 20060109
ABSTRACT:
One aspect of the present invention relates to water-sol. biphenylsulfonate ligands, i.e. sodium 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl-3'-sulfonate (I) (Cy = cyclohexyl) and sodium 2'-(dicyclohexylphosphanyl)-2,6-diisopropylbiphenyl-4-sulfonate (II) for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various 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 (in particular less reactive aryl chlorides), no. of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aq. solvent systems. Thus, 3,4-dimethylchlorobenzene (0.140 mL, 1.00 mmol) was coupled with phenylboronic acid (157 mg, 1.20 mmol) in the presence of Pd(OAc)2 (4.5 mg, 0.020 mmol, 2 mol%) and I (20.0 mg, 0.040 mmol, 4 mol% ), and K2CO3 (276 mg, 2.00 mmol) in water (1.0 mL) at room temp. for 10 h to give 1 3,4-dimethylbiphenyl as a colorless oil (151 mg, 99% yield).
Updated 5/11/2007 8:54:48 AM
