Reference

Process for producing aminobiaryl and aminoalkylbiaryl compound by nickel-catalyzed coupling of arylboronic acid with haloarylamine

All Rights Reserved. Process for producing aminobiaryl and aminoalkylbiaryl compound by nickel-catalyzed coupling of arylboronic acid with haloarylamine. Sato, Koichi; Miki, Takashi; Ueda, Hiroshi (Sumitomo Chemical Company, Limited, Japan). PCT Int. Appl. WO 2007011005 A1 25 Jan 2007, 65pp. DESIGNATED STATES: 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, HN, HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR, KZ, LA, 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, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN; RW: AT, BE, BF, BJ, CF, CG, CH, CI, CM, CY, DE, DK, ES, FI, FR, GA, GB, GR, IE, IS, IT, LU, MC, ML, MR, NE, NL, PT, SE, SN, TD, TG, TR. (Japanese). (World Intellectual Property Organization). CODEN: PIXXD2. APPLICATION: WO 2006-JP314438 14 Jul 2006. PRIORITY: JP 2005-209531 20 Jul 2005. DOCUMENT TYPE: Patent CA Section: 25 (Benzene, Its Derivatives, and Condensed Benzenoid Compounds) A process for producing a biaryl compd. of formula Y-Ar1-Ar2-Z [Ar1, Ar2 = each (un)substituted arylene or heteroarylene; or substituents of the adjacent carbon atoms on the arylene and heteroarylene groups are bonded together to form a fused ring; Y, Z = H, NH2, aminoalkyl; provided that both Y and Z are not simultaneously H and the alkyl of the aminoalkyl is optionally substituted by CO2H or alkoxycarbonyl] comprises reacting an arom. org. compd. of formula Y-Ar1-X (Ar1, Y = same as above; X = halo, alkylsulfonyloxy, arylsulfonyloxy) with at least one compd. selected from the group consisting of an arom. organoboron compd. of formula Z-Ar2-B(Q1)Q2 (Z, Ar2 = same as above; Q1, Q2 = HO, C1-4 alkoxy; or Q1 and Q2 are bonded together to represent C1-6 alkylenedioxy or catechol) and a boroxin ring compd. (I) (Z, Ar2 = same as above) in the presence of a zero-valence nickel catalyst, a phosphine ligand and a base.There are some commonly used reagents with their cas registry numbers 95-51-2 and 128796-39-4 in this article. This coupling reaction efficiently proceeds without lowering the catalyst activity in spite of the presence of an amino group in reactants. Thus, phenylboronic acid 209, 2-chloroaniline 168, bis(1,5-cyclooctadiene)nickel 18, tricyclohexylphosphine 37 mg, K3PO4 (1.00 g), distd. water (931 mg), and 3 mL 1,4-dioxane were mixed and the resulting mixt. was heated to 85° and stirred for 4 h to give 81% 2-aminobiphenyl. .