Trichlorosilane → HCID 18414905, compound

HRID 376941Notes

Reaction equation

HRID 376941 reaction equation
[C:1]1([P:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[C:19]2[C:28]3[C:23](=[CH:24][C:25]([Br:29])=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[OH:30])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[SiH](Cl)Cl>O1CCOCC1>[C:31]1([P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[C:19]2[C:28]3[C:23](=[CH:24][C:25]([Br:29])=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[OH:30])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 24811TrichlorosilaneHCID 18414911HCID 18414911, compound2×

Product 1

HCID 18414905HCID 18414905, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An optically active binaphthol (VII) as a starting material is reacted by a method described in the literature (M. Vondenhof and J. Mattay, Tetrahedron Lett., 1990, Vol. 31, pp. 985-988; L. Kurz, G. Lee, D. Morgans, Jr., M. J. Waldyke, and T. Ward, Tetrahedron Lett., 1990, Vol. 31, pp. 6321-6324) and by a method described in the literature (Y. Uozumi, A. Tanahashi, S.-Y. Lee, and T. Hayashi, J. Org. Chem., 1993, Vol. 58, pp. 1945-1948). That is, the binaphthol (VII) is reacted with trifluoromethanesulfonic anhydride (Tf2O) using pyridine in methylene chloride to convert compound (VII) to 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl (VIII), which is reacted with diphenylphosphine oxide (Ph2PHO) in the presence of a catalytic amount of a palladium-phosphine complex, whereby 2'-diphenylphosphinyl-2-trifluoromethanesulfonyloxy-1,1'-binaphthyl (IX) can be synthesized. Compound (IX) is hydrolyzed with lithium hydroxide (LiOH) to obtain 2'-diphenylphosphinyl-2-hydroxy-1,1'-binaphthyl (X), which is brominated in dioxane to obtain 2'-diphenylphosphinyl-2-hydroxy-6-bromo-1,1'-binaphthyl (XI). Compound (XI) is reduced with trichlorosilane (HSiCl3) to obtain 2'-diphenylphosphino-2-hydroxy-6-bromo-1,1'-binaphthyl (XII), which is reacted with 2-vinyl-5,5-dimethyl-1,3-dioxa-2-borinane using a palladium catalyst by a method described in the literature (Y. Miyaura and A. Suzuki, J. C. S. Chem. Commun., 1979, p. 866) to obtain 2'-diphenylphosphino-2-hydroxy-6-vinyl-1,1'-binaphthyl (XIII).

Sources & evidence

ORD record
ord-10d11903c3494acaa3e4aefc9021a0ee
Source dataset
uspto-grants-2000_02
Patent number
US06022936

Reaction notes

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