Diisooctyl phthalate → Triphenylphosphine

HRID 1045037

Reaction equation

HRID 1045037 reaction equation
CC(CCCCCOC([C:12]1[C:17](C(OCCCCCC(C)C)=O)=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)C.[CH:29]1[CH:30]=[CH:31][C:32]([P:35](C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:33][CH:34]=1.C1OC2C(C3C4OCOC=4C=CC=3P(C3C=CC=CC=3)C3C=CC=CC=3)=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2O1.C1C2C=CC(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2)CCC2C=CC(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2)C1.COC1C(P(C2C=CC=CC=2)CCP(C2C(OC)=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.CC(C(C)P(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(CC2C(CP(C3C=CC=CC=3)C3C=CC=CC=3)OC(C)(C)O2)C2C=CC=CC=2)C=CC=CC=1.ClC1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C(C2C(OC)=C(Cl)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=1OC.CC1P(C2C(P3C(C)CCC3C)=CC=CC=2)C(C)CC1.C1(P(C2C=CC=CC=2)C(CC(P(C2C=CC=CC=2)C2C=CC=CC=2)C)C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)CNC2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2CNC(CP(C3C=CC=CC=3)C3C=CC=CC=3)C2)C=CC=CC=1>>[CH:39]1[CH:38]=[CH:37][C:36]([P:35]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:32]2[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=2)=[CH:41][CH:40]=1

Participants

13

Reactant 12

HCID 33934Diisooctyl phthalate2×HCID 122582((5-((Diphenylphosphino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)(diphenyl)phosphineHCID 634876Binap, (A+-)-3×HCID 27345571,2-Bis[(2-methoxyphenyl)phenylphosphino]ethane3×HCID 3882352Chiraphos3×HCID 41858942,4-Bis(diphenylphosphino)pentaneHCID 41875183,4-bis(diphenylphosphino)-PyrrolidineHCID 41893931,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzeneHCID 50000714-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-PyrrolidineHCID 5165044(5,5'-Dichloro-6,6'-dimethoxy-2,2'-biphenyldiyl)bis(diphenylphosphine)HCID 10864772(R)-Phanephos2×HCID 110175104,4'-Bi-1,3-benzodioxole-5,5'-diylbis(diphenylphosphine)3×

Product 1

HCID 11776Triphenylphosphine

Procedure

Synthesis of Complexes using C2 symmetric bis-P ligands (DIOP, BINAP, Cl-MeO-BIPHEP, SEGPHOS, PhanePHOS, DIPAMP, DuPHOS, BDPP, CHIRAPHOS, PPM, PYRPHOS) uses the compound [RuCl2(benzene)], RuCl2(PPh3)3 and trans-RuCl2(NBD)(py)2 as the starting material, while the complexes were prepared in accordance with the procedure published in the literature (Noyori, R.; Takeshi, O.; Hirohito, O. Shohei, H.; Takao, I. J. Am. Chem. Soc. 1995, 117, 2675; Akotsi, O. M.; Meters, K.; Reid, R. D.; McDonald, R.; Bergens, S. H. Chirality 2000, 12, 514-522; BINAP=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, DIOP=4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, Cl-MeO-BIPHEP=5,5′-Dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl, SEGPHOS=5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, PhanePHOS=4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane, DIPAMP=1,2-Bis[(2-methoxyphenyl)(phenyl)phosphino]ethane, Me-DuPHOS=1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene, BDPP=2,4-Bis(diphenylphosphino)pentane, CHIRAPHOS=Bis(diphenylphosphino)butane, PYRPHOS=3,4-bis(diphenylphosphino)-Pyrrolidine, PPM=4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-Pyrrolidine. Synthesis of Complexes using C1 symmetric bis-P ligand (JosiPHOS, WalPHOS, MandyPHOS) uses the compound RuCl2(PPh3)3 as the starting material which can be obtained easily from hydrated RuCl3 and PPh3 (Steohenson, T. A.; Wilkinson, G. J. Inorg. Nucl. Chem. 1966, 28, 945-956; Josiphos=1-[Diarylphosphano]-2-[1-(dicyclohexylphosphano)ethyl]ferrocene.), while the complexes and RuCl2[(R,S)-Josiphos](PPh3) were prepared in accordance with the procedure published in the literature (Baratta, W.; Ballico, M.; Chelucci, G.; Siega, K.; Rigo, P. Angew. Chem. Int. Ed. 2008, 47, 4362-4365). The monochloride complex (11) was prepared from (10) by reacting with Et3N. The pre-catalysts used for in situ hydrogenation were [RuCl2BINAP(pyridine)2, RuCl2DIOP(pyridine)2, RuCl2(Josiphos)(pyridine)2]. As non-limiting examples of the present invention the synthesis and the characteristics of the complexes (8-25) are described in detail. All the syntheses were carried out under argon atmosphere, using freshly distilled solvents.

Workup

  1. customSynthesis of Complexes
  2. customwhile the complexes were prepared in accordance with the procedure
  3. customSynthesis of Complexes

Sources & evidence

ORD record
ord-ee399126a4ea4fbb8e6c2d6923800d12
Source dataset
uspto-grants-2013_10
Patent number
US08563739B2

Linked notes

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