New fluorous tagging and scavenging reactants and methods of synthesis and use thereof

A method for increasing the fluorous nature of an organic compound, comprising:

• reacting the organic compound with at least one second compound having the formula:
• XCO2CH2Rd
• to create a first fluorous tagged organic compound, wherein X is a leaving group and Rd is selected from the group consisting of:
• a) —CH═CH—(CH2)nRf,
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• c) —C6H5-m″[Wp(CH2)nRf]m″,
• wherein Rf and Rf′ are each fluorous groups, m is an integer from 1 to 4, m′ is an integer from 0 to 4, m″ is an integer from 1 to 5, n and n′ are each integers from 0 to 5, p and p′ each have a value of 0 or 1, and W and W′ are groupings of atoms each selected from the group consisting of O, S, NR25, CR26R27, and SiR28R29, wherein R25, R26 and R27 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R28 and R29 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf,
• the organic compound having at least one functional group reactive with group X on the second compound forming at least one chemical bond between the organic compound and the second compound resulting in the first fluorous tagged organic compound wherein the fluorous nature of the first fluorous tagged organic compound is increased relative to the organic compound to enable separation of the first fluorous tagged organic compound from at least one other compound by using a fluorous separation technique.

A method for increasing the fluorous nature of an organic compound, comprising:

• reacting the organic compound with at least one fluorous nitrogen containing compound having the formula:
• R31R32N(CH2)nRf
• to create a first fluorous tagged organic compound, wherein n is an integer from 0 to 5, Rf is a fluorous group, and R31R32 is selected from the group consisting of:
• a) —(CH2)mW(CH2)m′—, wherein m and m′ are each integers between 2 and 4, W is one of CH2, O, S, NH, and NR33, wherein R33 is one of a linear alkyl, a branched alkyl and a benzyl group,
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• wherein m″, and m′″ are each integers from 0 to 3,
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• wherein W′ is a grouping of atoms selected from the group consisting of O, S, NR34, CR35R36, and SiR37R38, p has a value of 0 or 1, n′ is an integer from 0 to 5, m″″ is an integer from 0 to 4, R34, R35, and R36 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R37 and R38 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf,
• d) alkyl and pyridyl,
• e) hydrogen and —(CH2)n″NH2, wherein n″ is an integer from 1 to 5,
• f) hydrogen and —(CH2)n″N[(CH2)n″NH2]2, and
• g) —(CH2)n′″OH, and —(CH2)n″″OH, wherein n′″ and n″″ are each integers between 1 and 5,
• the organic compound having at least one functional group reactive with at least one N or —OH group on the second compound forming at least one chemical bond between the organic compound and the second compound resulting in the first fluorous tagged organic compound wherein the fluorous nature of the first fluorous tagged organic compound is increased relative to the organic compound to enable separation of the first fluorous tagged organic compound from at least one other compound by using a fluorous separation technique.

A method for increasing the fluorous nature of an organic compound, comprising:

• reacting the organic compound with at least one second compound having the formula:
• X—C6H5-m—[Wp(CH2)nRf]m
• to create a first fluorous tagged organic compound, wherein Rf is a fluorous group, m is an integer from 1 to 5, n is an integer from 0 to 5, p has a value of 0 or 1, and W is a grouping of atoms selected from the group consisting of O, S, NR39, CR40R41, and SiR42R43,
• wherein when W is O, X is a grouping of atoms selected from the group consisting of —SO2NHNH2, —CHO when p is 1, —SH, —(CH2)n′SH, —C(═NRB)C6H4Y, —C(═O)CH2C(═O)R44, —COCl, —SO2Cl, —OH, —NCZ, and —SO3H,
• wherein when W is one of S, NR39, CR40R41, and SiR42R43, X is a grouping of atoms selected from the group consisting of —SO2NH2, —SO2NHNH2, —CHO when p is 1, —SH, —(CH2)n″SH, —C(═NRB)C6H4Y, —C(═O)CH2C(═O)R44, —COCl, —SO2Cl, —OH, —NCZ, and —SO3H,
• wherein n′ is an integer from 2 to 5, r is an integer from 0 to 2, Z is one of O and S, Y is one of an electron withdrawing group, a hydrogen and an alkyl group, RB is one of hydrogen, alkyl, aryl and hydroxyl, R44 is one of linear alkyl, branched alkyl and benzyl, R39, R40 and R41 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R42 and R43 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf,
• the organic compound having at least one functional group reactive with group X on the second compound forming at least one chemical bond between the organic compound and the second compound resulting in the first fluorous tagged organic compound wherein the fluorous nature of the first fluorous tagged organic compound is increased relative to the organic compound to enable separation of the first fluorous tagged organic compound from at least one other compound by using a fluorous separation technique.

A method for increasing the fluorous nature of an organic compound, comprising:

• reacting the organic compound with at least one second compound having the formula:
• X—(CH2)nRf
• to create a first fluorous tagged organic compound, wherein Rf is a fluorous group, n is an integer from 0 to 5, and X is a grouping of atoms selected from the group consisting of —C(CH3)2COCl, —CR45R46 SH, —CR45R46SR47, —SO2Cl, —OC(═O)NHNH2, —NHC(═NH)NH2, —SO2NH2, —SO2NHNH2, —NCZ, -maleimide, -α-succinic anhydride, and —COCH2COR48, wherein Z is one of O and S, and R45, R46, R47, and R48 are independently, the same or different, selected from the group consisting of hydrogen, linear alkyl, branched alkyl, benzyl, and —(CH2)nRf,
• the organic compound having at least one functional group reactive with group X on the second compound forming at least one chemical bond between the organic compound and the second compound resulting in the first fluorous tagged organic compound wherein the fluorous nature of the first fluorous tagged organic compound is increased relative to the organic compound to enable separation of the first fluorous tagged organic compound from at least one other compound by using a fluorous separation technique.

A compound for increasing the fluorous nature of an organic compound, the compound having the formula:

• XCO2CH2Rd
• wherein X is a leaving group and Rd is selected from the group consisting of:
• a) —CH═CH—(CH2)nRf,
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• c) —C6H5-m″[Wp(CH2)nRf]m″,
• wherein Rf and Rf′ are fluorous groups, m is an integer from 1 to 4, m′ is an integer from 0 to 4, m″ is an integer from 1 to 5, n and n′ are each integers from 0 to 5, p and p′ each have a value of 0 or 1, and W and W′ are groupings of atoms each selected from the group consisting of O, S, NR25, CR26R27 and SiR28R29, wherein R25, R26 and R27 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R28 and R29 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf.

A fluorous nitrogen containing compound having the formula:

• R31R32N(CH2)nRf
• wherein n is an integer from 0 to 5, Rf is a fluorous group, and R31R32 is selected from the group consisting of:
• a) —(CH2)mW(CH2)m′—, wherein m and m′ are each integers between 2 and 4, W is one of CH2, O, S, NH, and NR33, wherein R33 is one of a linear alkyl, a branched alkyl and a benzyl group,
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• wherein m″ and m′″ are each integers from 0 to 3,
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• wherein W′ is a grouping of atoms selected from the group consisting of O, S, NR34, CR35R36, SiR37R38, p has a value of 0 or 1, n′ is an integer from 0 to 5, m″″ is an integer from 0 to 4, R34, R35, and R36 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R37 and R38 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf,
• d) alkyl and pyridyl,
• e) hydrogen and CH2)n″NH2, wherein n″ is an integer from 1 to 5,
• f) hydrogen and —(CH2)n″N[(CH2)n″NH2]2, and
• g) —(CH2)n′″OH, and —(CH2)n″″OH, wherein n′″ and n″″ are each integers between 1 and 5.

A compound for increasing the fluorous nature of an organic compound, the compound having the formula:

• X—C6H5-m—[Wp(CH2)nRf]m
• wherein Rf is a fluorous group, m is an integer from 1 to 5, n is an integer from 0 to 5, p has a value of 0 or 1, and W is a grouping of atoms selected from the group consisting of O, S, NR39, CR40R41, and SiR42R43
• wherein when W is O, X is a grouping of atoms selected from the group consisting of —SO2NHNH2, —CHO when p is 1, —SH, —CH2)n′SH, —C(═NRB)C6H4Y, —C(═O)CH2C(═O)R44,
• wherein when W is one of S, NR39, CR40R41, and SiR42R43, X is a grouping of atoms selected from the group consisting of-SO2NH2, —SO2NHNH2, —CHO when p is 1, —SH, —(CH2)n′SH, —C(═NRB)C6H4Y, and —C(═O)CH2C(═O)R44,
• wherein Y is one of an electron withdrawing group, a hydrogen and an alkyl group, RB is one of hydrogen, alkyl, aryl and hydroxyl, R44 is one of linear alkyl, branched alkyl and benzyl, R39, R40 and R41 are independently, the same or different, one of hydrogen, linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf, and R42 and R43 are independently, the same or different, one of linear alkyl, branched alkyl, aryl, benzyl and —(CH2)nRf.