Trichlorosilane → 2'-(Diphenylphosphino)[1,1'-binaphthalen]-2-ol

HRID 260998Notes

Reaction equation

HRID 260998 reaction equation
[C:1]1([P:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[O:29]S(C(F)(F)F)(=O)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[SiH](Cl)Cl>C(N(CC)CC)C>[C:37]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][C:20]=2[OH:29])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 24811TrichlorosilaneHCID 104385762'-Diphenylphosphinyl-2-trifluoromethanesulfonyloxy-1,1'-binaphthyl

Product 1

HCID 37366712'-(Diphenylphosphino)[1,1'-binaphthalen]-2-ol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

More specifically, 1,1'-bi-2-naphthol 10 is reacted with trifluoromethanesulfonic acid anhydride to obtain 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthYl 11 which is then reacted with diphenylphosphine oxide in the presence of a palladium complex catalyst to obtain 2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl 12. The compound 12 is reduced by trichlorosilane in the presence of triethylamine and then hydrolyzed to obtain 2-diphenylphosphino-2'-hydroxy-l,l'-binaphthyl 13. The compound 13 is reacted with a separately synthesized chlorophosphite 14 in the presence of triethylamine to obtain phosphine compound 15 of the present invention.

Sources & evidence

ORD record
ord-4922753f4e6044ee979e3f68e48c018e
Source dataset
uspto-grants-1996_06
Patent number
US05530150

Reaction notes

Loading…