Fluorination of organic compounds
Methods for fluorinating organic compounds are described herein.
1. A compound of formula (I):
wherein
R 1 and R 2 are each independently selected from C 6-12 aryl, C 6-12 aralkyl, 6-12 membered heteroaryl, 6-12 membered heteroaralkyl, 6-12 membered heterocyclyl and 6-12 membered heterocyclylalkyl, each of which is substituted with 0-3 occurrences of R 5 ;
X is an optionally substituted C 2 -C 5 alkenylene moiety
each R 5 is independently selected from halo, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 6-12 aryl and 6-12 membered heteroaryl.
2. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from C 6-12 aryl, 6-12 membered heteroaryl and 6-12 membered heterocyclyl.
3. The compound of claim 1 , wherein X is an optionally substituted C 2 alkenylene.
4. The compound of claim 1 , wherein the compound of formula (I) is a compound of formula (Ia):
wherein
each R 3 is independently selected from C 1-8 alkyl, nitro, cyano, halo, C 1-8 haloalkyl, C 1-8 alkoxy, C 6-12 aryl, C 6-12 aralkyl, 6-12 membered heteroaryl, 6-12 membered heterocyclyl and 6-12 membered heterocyclylalkyl; and
n is 0, 1 or 2.
5. The compound of claim 1 , wherein the compound of formula (I) is a compound of formula (Ib):
6. The compound of claim 1 , wherein each R 5 is independently selected from C 1-8 alkyl, C 1-8 haloalkyl and C 1-8 alkoxy.
7. The compound of claim 1 , wherein the compound of formula (I) is a compound of formula (Ic):
8. A method of producing a compound of claim 1 , the method comprising reacting a compound of formula (II):
wherein R 1 , R 2 and X are as defined in claim 1 ; wherein
LG is a leaving group; and
Q is an anion;
with a fluorine source to produce the compound of formula (I).
9. The method of claim 8 , wherein R 1 and R 2 are each independently selected from C 6-12 aryl, 6-12 membered heteroaryl and 6-12 membered heterocyclyl.
10. The method of claim 8 , wherein X is an optionally substituted C 2 alkenylene.
11. The method of claim 8 , wherein each R 5 is independently selected from C 1-8 alkyl, C 1-8 haloalkyl and C 1-8 alkoxy.
12. The method of claim 8 , wherein the fluorine source is F − or a salt thereof.
13. A reaction mixture comprising a compound of claim 1 , an organic compound and a fluorine source.
14. A composition comprising a compound of formula (I) and an additional component
wherein
R 1 and R 2 are each independently selected from C 6-12 aryl, C 6-12 aralkyl, 6-12 membered heteroaryl, 6-12 membered heteroaralkyl, 6-12 membered heterocyclyl and 6-12 membered heterocyclylalkyl, each of which is substituted with 0-3 occurrences of R 5 ;
each R 5 is independently selected from halo, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 6-12 aryl and 6-12 membered heteroaryl;
X is an optionally substituted C 2 -C 5 alkenylene moiety.