Method for preparing iodosilanes
Provided is methodology for the preparation of highly-desired iodosilanes such as H 2 SiI 2 and HSi 3 , via a reaction of alkylaminosilanes with certain substituted acid iodides. In one embodiment, bis(diethylamino)silane is reacted with benzoyl iodide to provide diiodosilane.
1. A method for preparing a compound having the formula (I):
(H) x Si(I) y (I);
wherein x is 1 or 2, y is 2 or 3, and the sum of x plus y is 4, the method comprising:
contacting a compound of the formula (A):
(H) x Si(N(R 1 )(R 2 )) y (A);
wherein (i) each R 1 and each R 2 is independently chosen from a C 1 -C 6 alkyl group, a C 3 -C 8 cycloaliphatic group, or hydrogen, or (ii) R 1 and R 2 are taken together with the nitrogen atom to which they are bonded to form a C 4 -C 7 nitrogen-containing saturated or aromatic ring, provided that no more than one of R 1 and R 2 is hydrogen;
with a compound of the formula:
wherein R 3 is chosen from C 1 -C 6 alkyl, C 1 -C 6 substituted alkyl, benzyl, substituted benzyl, biphenyl, naphthyl, phenyl, or substituted phenyl,
to produce a compound of formula (I).
2. The method of claim 1 , wherein the compound of formula (I) is H 2 SiI 2 .
3. The method of claim 1 , wherein the compound of formula (I) is HSiI 3 .
4. The method of claim 1 , wherein R 1 and R 2 are chosen from methyl, ethyl, propyl, sec-butyl, and t-butyl.
5. The method of claim 1 , wherein at least one of R 1 and R 2 is t-butyl.
6. The method of claim 1 , wherein at least one of R 1 and R 2 is cyclohexyl.
7. The method of claim 1 , wherein R 1 and R 2 are taken together with the nitrogen atom to which they are attached, to form a pyrrole, pyrrolidine, or piperidine ring.
8. The method of claim 1 , wherein R 3 is C 1 -C 6 alkyl.
9. The method of claim 1 , wherein R 3 is phenyl.
10. The method of claim 1 , wherein R 3 is substituted phenyl.
11. The method of claim 10 , wherein R 3 is 4-fluorophenyl.
12. The method of claim 10 , wherein R 3 is 3,5-difluorophenyl.
13. The method of claim 1 , wherein at least one of R 1 and R 2 is ethyl and R 3 is methyl or phenyl.
14. A method for preparing a compound having the formula (II):
(H) z (I) y Si—Si(I) y (H) z (II)
wherein y is 2 or 3, z is 0 or 1, and the sum of y and z is 3, the method comprising:
contacting a compound of the formula (B):
H z ((R 1 )(R 2 )N) y Si—Si(N(R 2 )(R 1 )) y H z (B);
wherein (i) each R 1 and each R 2 is independently chosen from a C 1 -C 6 alkyl group, a C 3 -C 8 cycloaliphatic group, or hydrogen, or (ii) R 1 and R 2 are taken together with the nitrogen atom to which they are bonded to form a C 4 -C 7 nitrogen-containing saturated or aromatic ring, provided that no more than one of R 1 and R 2 is hydrogen;
with a compound of the formula:
wherein R 3 is chosen from C 1 -C 6 alkyl, C 1 -C 6 substituted alkyl, benzyl, substituted benzyl, biphenyl, naphthyl, phenyl, or substituted phenyl,
to produce a compound of formula (II).
15. The method of claim 14 , wherein R 1 and R 2 are chosen from methyl, ethyl, propyl, sec-butyl, and t-butyl.
16. The method of claim 14 , wherein at least one of R 1 or R 2 is t-butyl.
17. The method of claim 14 , wherein at least one of R 1 or R 2 is cyclohexyl.
18. The method of claim 14 , wherein R 1 and R 2 are taken together with the nitrogen atom to which they are attached, to form a pyrrole, pyrrolidine, or piperidine ring.
19. The method of claim 14 , wherein R 3 is C 1 -C 6 alkyl.
20. The method of claim 14 , wherein R 3 is phenyl.
21. The method of claim 14 , wherein at least one of R 1 and R 2 is ethyl and R 3 is methyl or phenyl.