Perfluorosulfonylmethide compounds; use thereof for carbon-carbon bond formation
AssigneeThe Institute of Applied Catalysis
InventorsAnthony Gerard Martin Barrett, David Christopher Braddock, David Chadwick
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Abstract
Free perfluorosulfonylmethide compounds and metal salts thereof show strong catalytic activity in carbon-carbon bond formation reactions, in amounts as low as 0.1 mole %. Fluorous media may be used, especially biphasic fluorous media enabling ready recycling of the catalyst. The formula thereof is: M[C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q]x where M is H, Sc, Y, La, Ce, Pr, Nd, Sm Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl, x is the common oxidation state of a said metal M, R1, R2 and R3 are perfluorinated or polyfluoronated hydrocarbon, ether or amine moieties or mixtures thereof and m+q=0, 1, 2 or 3 (m and q being zero or integers).
Claims22
In a process involving a catalyzed carbon-carbon bond formation, the improvement wherein the catalyst is a fluorosulfonylmethide compound represented by the formula I:
- M[C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q]x
- where
- M is H, Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl
- x is the common oxidation state of a said metal M
- R1, R2 and R3 are perfluorinated or polyfluorinated hydrocarbon, ether or amine moieties or mixtures thereof
- and m+q=0, 1 2 or 3 (m and q being zero or integers).
A compound of the formula I
- M[C(SO2R1)3−(M+g)(SO2R2)m (SO2R3)g]x
- where
- M is H, Sc, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl
- x is the common oxidation state of a said metal M
- R1, R2 and R3 are perfluorinated or polyfluorinated hydrocarbon, ether or amine moieties or mixtures thereof
- and m+g=0, 1, 2 or 3 (m and q being zero or integers) with the exclusion of compounds where M is H, Yb or Sc, and m and q are zero and R1=CF3.
A compound of the formula I
- M[C(SO2R1)3−(M+g)(SO2R2)m (SO2R3)g]x
- where
- M is H, Sc, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl
- x is the common oxidation state of a said metal M
- R1, R2 and R3 are perfluorinated or polyfluorinated hydrocarbon, ether or amine moieties or mixtures thereof
- and m+g=0, 1, 2 or 3 (m and g being zero or integers) with the further proviso that R1, R2 and R3 and perfluorinated hydrocarbon moieties, and m and g are zero and R1 is C4F9, C6F13 or C8F17.
A mixed-ligand compound of the formula I
- M[C(SO2R1)3−(M+g)(SO2R2)m (SO2R3)g]x
- where
- M is H, Sc, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl
- x is the common oxidation state of a said metal M
- R1, R2 and R3 are perfluorinated or polyfluorinated hydrocarbon, ether or amine moieties or mixtures thereof
- and m+g=0, 1, 2 or 3 (m and g being zero or integers) with the further proviso that R1, R2 and R3 and perfluorinated hydrocarbon moieties, and m is 1, g is zero, R2 or R1 is C6F13 and R1 or R2 is C8F17.
Dependencies are inferred from the claim text.