Pentafluorosulfanyl pyridine
A pyridine compound having a SF 5 group on position-3 and position-4 of a pyridine ring is provided. Pentafluorosulfanyl pyridine represented by formula (d): wherein a SF 5 group binds to either one of position-3 or position-4 of a pyridine ring, and R 2 binds to the other one of position-3 or position-4; and R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom, a halogen atom, a substituted or non-substituted alkyl group having 1 to 18 carbon atoms, a substituted or non-substituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or non-substituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or non-substituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 18 carbon atoms, a substituted or non-substituted aryloxy group having 6 to 30 carbon atoms, an acyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted alkanesulfonyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted arenesulfonyloxy group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or non-substituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, an amino group, an azide group, a substituted or non-substituted aralkyloxy group having 7 to 30 carbon atoms, a substituted or non-substituted aralkylsulfide group having 7 to 30 carbon atoms, or a SF 5 group.
1. Pentafluorosulfanyl pyridine represented by formula (d):
wherein a SF 5 group binds to either one of position-3 or position-4 of a pyridine ring, and R 2 binds to the other one of position-3 or position-4; and
R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom, a halogen atom, a substituted or non-substituted alkyl group having 1 to 18 carbon atoms, a substituted or non-substituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or non-substituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or non-substituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 18 carbon atoms, a substituted or non-substituted aryloxy group having 6 to 30 carbon atoms, an acyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted alkanesulfonyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted arenesulfonyloxy group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or non-substituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, an amino group, an azide group, a substituted or non-substituted aralkyloxy group having 7 to 30 carbon atoms, a substituted or non-substituted aralkylsulfide group having 7 to 30 carbon atoms, or a SF 5 group), wherein at least one of the R 1 and R 4 is a fluorine atom.
2. Pentafluorosulfanyl pyridine according to claim 1 that is 2-fluoro-3-pentafluorosulfanyl pyridine, 2,6-difluoro-3-pentafluorosulfanyl pyridine, or 6-fluoro-3-pentafluorosulfanyl pyridine.
3. Chlorotetrafluorosulfanyl pyridine represented by formula (c′):
wherein a SF 4 Cl group binds to either one of position-3 or position-4 of a pyridine ring, and R 2 binds to the other one of position-3 or position-4; and
R 1 , R 2 , R 3 , and R 4 are independently a hydrogen atom, a halogen atom, a substituted or non-substituted alkyl group having 1 to 18 carbon atoms, a substituted or non-substituted aryl group having 6 to 30 carbon atoms, a nitro group, a cyano group, a substituted or non-substituted alkanesulfonyl group having 1 to 18 carbon atoms, a substituted or non-substituted arenesulfonyl group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 18 carbon atoms, a substituted or non-substituted aryloxy group having 6 to 30 carbon atoms, an acyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted alkanesulfonyloxy group having 1 to 18 carbon atoms, a substituted or non-substituted allenesulfonyloxy group having 6 to 30 carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 18 carbon atoms, a substituted or non-substituted aryloxycarbonyl group having 7 to 30 carbon atoms, a substituted carbamoyl group having 2 to 18 carbon atoms, a substituted amino group having 1 to 18 carbon atoms, an amino group, an azide group, a substituted or non-substituted aralkyloxy group having 7 to 30 carbon atoms, a substituted or non-substituted aralkylsulfide group having 7 to 30 carbon atoms, or a SF 5 group).
4. Chlorotetrafluorosulfanyl pyridine according to claim 3 , wherein at least one of the R 1 and R 4 is a fluorine atom.
5. Chlorotetrafluorosulfanyl pyridine according to claim 3 that is 2-fluoro-3-chlorotetrafluorosulfanyl pyridine, 2,6-difluoro-3-chlorotetrafluorosulfanyl pyridine, or 6-fluoro-3-chlorotetrafluorosulfanyl pyridine.
6. A manufacturing process of pentafluorosulfanyl pyridine according to claim 1 comprising:
a step of reacting a pyridyldisulfide compound represented by formula (a):
wherein R 1 , R 2 , R 3 , and R 4 are as defined above,
with halogens selected from a group consisting of chlorine, bromine, iodine and a halogen compound, and
a fluoride salt represented by formula (b):
M + F − (b)
wherein M is a metal atom, an ammonium group or a phosphonium group
to form halotetrafluorosulfanyl pyridine represented by formula (c):
wherein R 1 , R 2 , R 3 , and R 4 are as defined above, and X is a chlorine atom, a bromine atom or an iodine atom; and
a step of reacting the halotetrafluorosulfanyl pyridine with a fluoride source to form pentafluorosulfanyl pyridine.
7. The process according to claim 6 , wherein a halogen to be reacted with pyridyldisulfide is chlorine (Cl 2 ).
8. The process according to claim 6 , wherein the fluoride salt represented by formula (b) is alkali metal fluoride.
9. The process according to claim 6 , wherein the fluoride source is hydrogen fluoride.