Electronically activated strained alkynes
Compounds of Formula I: wherein: R 1 and R 2 are hydrogen or C 1 to C 12 linear or branched alkyl; R 3 is hydrogen, C 1 to C 12 linear or branched alkyl, or nitrogen protecting groups; X is oxygen or nitrogen; and when X is oxygen, R 4 is absent; and when X is nitrogen, R 4 is C 1 to C 12 linear or branched alkyl or nitrogen protecting groups. The compounds are useful as reagents in 1,3-cycloaddition reactions.
1. Compounds of Formula I:
wherein:
R 1 and R 2 are independently selected from hydrogen and C 1 to C 12 linear or branched alkyl;
R 3 is selected from hydrogen, C 1 to C 12 linear or branched alkyl, and nitrogen protecting groups;
X is oxygen or nitrogen;
when X is oxygen, R 4 is absent; and
when X is nitrogen, R 4 is selected from C 1 to C 12 linear or branched alkyl and nitrogen protecting groups.
2. The compounds of claim 1 , wherein X is oxygen.
3. The compounds of claim 1 , wherein X is nitrogen.
4. The compounds of claim 3 , wherein R 4 is C 1 to C 12 linear or branched alkyl.
5. The compounds of claim 3 , wherein R 4 a nitrogen protecting group.
6. A compound of claim 1 , wherein one of R 1 or R 2 is C 1 to C 12 linear or branched alkyl.
7. The compounds of claim 6 , wherein X is oxygen.
8. The compounds of claim 6 , wherein X is nitrogen.
9. The compounds of claim 8 , wherein R 4 is C 1 to C 12 linear or branched alkyl.
10. The compounds of claim 8 , wherein R 4 a nitrogen protecting group.
11. A compound of claim 1 , wherein R 1 and R 2 are C 1 to C 12 linear or branched alkyl.
12. The compounds of claim 11 , wherein X is oxygen.
13. The compounds of claim 11 , wherein X is nitrogen.
14. The compounds of claim 13 , wherein R 4 is C 1 to C 12 linear or branched alkyl.
15. The compounds of claim 13 , wherein R 4 a nitrogen protecting group.
16. A compound of claim 1 , wherein one of R 1 or R 2 is C 1 to C 6 linear or branched alkyl.
17. The compounds of claim 16 , wherein X is oxygen.
18. The compounds of claim 16 , wherein X is nitrogen.
19. The compounds of claim 18 , wherein R 4 is C 1 to C 12 linear or branched alkyl.
20. The compounds of claim 18 , wherein R 4 a nitrogen protecting group.
21. A compound of claim 1 , wherein R 1 and R 2 are C 1 to C 6 linear or branched alkyl.
22. The compounds of claim 21 , wherein X is oxygen.
23. The compounds of claim 21 , wherein X is nitrogen.
24. The compounds of claim 23 , wherein R 4 is C 1 to C 12 linear or branched alkyl.
25. The compounds of claim 23 , wherein R 4 a nitrogen protecting group.
26. A method of forming chemical bonds, the method comprising reacting a first compound of Formula I:
wherein:
R 1 and R 2 are independently selected from hydrogen and C 1 to C 12 linear or branched alkyl;
R 3 is selected from hydrogen, C 1 to C 12 linear or branched alkyl, and nitrogen protecting groups;
X is oxygen or nitrogen;
when X is oxygen, R 4 is absent; and
when X is nitrogen, R 4 is selected from C 1 to C 12 linear or branched alkyl and nitrogen protecting groups;
with a second compound comprising a 1,3-dipole, in a 1,3-cycloaddition reaction.