Synthesis and use of fluorinated compounds
The invention is directed to the preparation of fluorinated compounds and their use in organic synthesis. In particular, the invention is directed to methods of reacting compounds of structure with R f —CH═N 2 or (CF 3 ) 2 C═N 2 to form a perfluoroalkylate or -arylated compounds, and products derived from these reactions, where X, Y B , and R f are described herein.
1. A compound of Formula Ia:
wherein
n is an integer from 1 to 50;
X is optionally substituted C 2-20 alkyl; optionally substituted C 1-20 heteroalkyl; optionally substituted C 2-20 alkenyl; optionally substituted C 2-20 alkynyl; optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, or fluorine; and
Y is —B-pinacol; —B(OR) 2 ; —BF 3 K; or BZ 2 ;
wherein each R is independently H or C 1-6 alkyl; and Z is halogen.
2. The compound of claim 1 , wherein n is 1 to 5.
3. The compound of claim 1 , wherein n is 6 to 10.
4. The compound of claim 1 , wherein n is 11 to 50.
5. The compound of claim 1 , wherein n is 1 or 2.
6. The compound of claim 1 , wherein n is 1.
7. The compound of claim 1 , wherein X is optionally substituted aryl.
8. The compound of claim 7 , wherein the aryl is optionally substituted phenyl, naphthyl, or fluorenyl.
9. The compound of claim 7 , wherein the aryl is substituted with 1, 2, or 3 substitutents independently selected from the group consisting of C 1-6 alkyl; C 1-6 alkenyl; C 1-6 alkynyl, —OC 1-6 alkyl; —OC 1-6 alkenyl; —C(O)C 1-6 alkyl; —C(O)-aryl; —C(O)-heteroaryl; —C(O)OC 1-6 alkyl; —C(O)O-aryl; —C(O)O-heteroaryl; —OC(O)C 1-6 alkyl; —OC(O)-aryl; —OC(O)-heteroaryl; aryl; heteroaryl; halogen; haloalkyl; nitro, —OH, —CN; or —SO 2 N(R 1 ) 2 , wherein each R 1 is independently H or —C 1-6 alkyl.
10. The compound of claim 1 , wherein X is:
11. The compound of claim 1 , wherein X is optionally substituted heteroaryl.
12. The compound of claim 11 , wherein the heteroaryl is furanyl, imidazolyl, pyrrolidinyl, pyrimidinyl, tetrazolyl, thienyl, pyridyl, pyrrolyl, N-methylpyrrolyl, quinolinyl, or isoquinolinyl.
13. The compound of claim 11 , wherein the heteroaryl is substituted with 1, 2, or 3 substitutents independently selected from the group consisting of C 1-6 alkyl; —C 1-6 alkenyl; —OC 1-6 alkyl; —OC 1-6 alkenyl; —C(O)C 1-6 alkyl; —C(O)-aryl; —C(O)-heteroaryl; —C(O)OC 1-6 alkyl; —C(O)O-aryl; —C(O)O-heteroaryl; —OC(O)C 1-6 alkyl; —OC(O)-aryl; —OC(O)-heteroaryl; aryl; heteroaryl; halogen; haloalkyl; nitro, —OH; —CN; or —SO 2 N(R 1 ) 2 , wherein each R 1 is independently H or —C 1-6 alkyl.
14. The compound of claim 11 , wherein X is:
15. The compound of claim 1 , wherein n is 1 or 2.
16. The compound of claim 1 , wherein n is 3 to 50.
17. The compound of claim 1 that is selected from the group consisting of:
18. The compound of claim 1 that is an isolated compound.