Preparation of secondary amines with electrophilic N-linchpin reagents
In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identical groups. Also provided herein are compositions for use in the preparation of the secondary amine.
1. A compound of the formula:
wherein:
X 1 and X 2 are each independently C, S, or S(O);
R 1 and R 2 are each isopropoxy; and
R 3 is a leaving group, wherein the leaving group is selected from the group consisting of halo, alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) ;
or a salt thereof.
2. The compound of claim 1 , wherein the compound is further defined as:
wherein:
R 1 and R 2 are isopropoxy; and
R 3 is a leaving group, wherein the leaving group is selected from the group consisting of halo, alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) ;
or a salt thereof.
3. The compound of claim 1 , wherein R 3 is a leaving group is selected from the group consisting of alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , and substituted arylsulfonyloxy (C≤12) .
4. The compound of claim 1 , wherein X 1 and X 2 are C.
5. The compound of claim 1 , wherein the compound is further defined as:
or a salt thereof.
6. The compound of claim 5 , wherein the compound is:
or a salt thereof.
7. The compound of claim 1 , wherein the compound is further defined as:
wherein:
R 1 and R 2 are each isopropoxy; and
R 3 is a leaving group, wherein alkylsulfonyl (C≤12) , substituted alkylsulfonyl (C≤12) , arylsulfonyl (C≤12) , substituted arylsulfonyl (C≤12) , alkylsulfonyloxy (C≤12) , substituted alkylsulfonyloxy (C≤12) , arylsulfonyloxy (C≤12) , or substituted arylsulfonyloxy (C≤12) ;
or a salt thereof.
8. The compound of claim 7 , wherein R 3 is arylsulfonyl (C≤12) or substituted arylsulfonyl (C≤12) .
9. The compound of claim 7 , wherein R 3 is alkylsulfonyloxy (C≤12) or substituted alkylsulfonyloxy (C≤12) .
10. The compound of claim 7 , wherein R 3 is arylsulfonyloxy (C≤12) or substituted arylsulfonyloxy (C≤12) .
11. The compound of claim 10 , wherein R 3 is arylsulfonyloxy (C≤12) .