Zwitterionic phosphonium salts
AssigneeThe Hong Kong Polytechnic University
InventorsTak-Hang Chan, Congde Huo, Xun He
Life of this patent
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Abstract
A zwitterionic phosphonium salt of Formula I: wherein n is 0 or 1; R is H or SO3; R′ is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, phenyl, substituted phenyl, benzyl and C1-C10 alkoxy-carbonyl; R′ is CX3 when n is O; and X is selected from the group consisting of F, Cl, Br and I. The zwitterionic phosphonium salts are useful reagents for the preparation of alkenes and acetals from the corresponding aldehyde.
Claims21
1-9. (canceled)
A zwitterionic phosphonium salt of Formula I:
- wherein:
- n is 0 or 1;
- R is SO3−;
- R′ is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, substituted phenyl, benzyl and C1-C10 alkoxycarbonyl when n is 1;
- R′ is CX3 when n is 0;
- and
- X is selected from the group consisting of F, Cl, Br and I.
A method for converting an aldehyde functionality into an alkene functionality, the method comprising reacting a substrate bearing an aldehyde functionality with a zwitterionic phosphonium salt of Formula I:
- wherein:
- n is 1;
- R is SO3−;
- and
- R′ is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, phenyl, substituted phenyl, benzyl and C1-C10 alkoxycarbonyl;
- in the presence of a base.
A method for converting an aldehyde functionality into an alkene functionality, the method comprising reacting a substrate comprising an aldehyde functionality with triphenylphosphine-meta-sulfonate, a compound comprising a halide or tosyl bound to a deprotonable carbon, and a base, in the presence of a solvent, to form a product mixture comprising an alkene product and a phosphine oxide by-product.
A method for converting an aldehyde functionality into an acetal functionality, the method comprising the step of reacting a substrate bearing an aldehyde functionality with a phosphonium salt of Formula I:
- wherein:
- n is 0 or 1;
- R is H or SO3−;
- R′ is a C1-C10 alkoxycarbonyl when n is 1;
- R′ is CX3 when n is 0;
- and
- X is selected from the group consisting of F, Cl, Br and I;
- in the presence of an alcohol.
A kit for converting an aldehyde functionality into an alkene functionality, comprising a zwitterionic phosphonium salt of Formula I:
- wherein:
- n is 1;
- R is SO3−;
- and
- R′ is selected from the group consisting of C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, phenyl, substituted phenyl, benzyl and C1-C10 alkoxycarbonyl;
- and
- instructions for use.
A kit for converting an aldehyde functionality into an acetal functionality, comprising a phosphonium salt of Formula I:
- wherein:
- n is 0;
- R is H or SO3−;
- R′ is CX3;
- and
- X is selected from the group consisting of F, Cl, Br and I;
- and
- instructions for use.
A kit for converting an aldehyde functionality into an alkene functionality comprising triphenylphosphine-meta-sulfonate, a compound comprising a halide or tosyl bound to a deprotonable carbon, and instructions for use.
Dependencies are inferred from the claim text.