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US 10,633,403 B2Granted
N-heterocyclic phosphines
AssigneeBoard of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada
InventorsJun Yong Kang, Karimulla Mulla, Kyle Aleshire, Paul M. Forster
Life of this patent
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Abstract
Provided herein are N-heterocyclic phosphines (NHPs) useful in metal-free phosphorus-carbon bond forming reactions. Methods for preparing vinylphosphonates using NHPs also are provided. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Claims20
A compound having a structure represented by a formula:
- wherein n is selected from 0 and 1;
- wherein p is selected from 0, 1, 2, 3, 4, and 5;
- wherein each of XA and XB is NR1;
- wherein each occurrence of R1, when present, is independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 cycloalkyl, 4-10 membered heterocycloalkyl, C6-C10 aryl, —(C1-C3 alkyl)(C6-C10 aryl), and 4-10 membered heteroaryl, and wherein each occurrence of R1, when present, is independently substituted with 0, 1, 2, 3, or 4 independently selected R5 groups;
- wherein Y is selected from O, S, and NR26;
- wherein R26, when present, is selected from hydrogen and C1-C8 alkyl;
- wherein Z is selected from C═S, S═O, and SO2;
- wherein each of RX and RY is independently selected from hydrogen, C1-C8 alkyl, C6-C10 aryl, and 4-10 membered heteroaryl, or wherein each of RX and RY are optionally covalently bonded together and, together with the intermediate carbon atoms, comprise a 5- to 7-membered cycloalkyl or 5- to 6-membered aryl;
- wherein R2 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 cycloalkyl, 4-10 membered heterocycloalkyl, C6-C10 aryl, —(C1-C3 alkyl)(C6-C10 aryl), and 4-10 membered heteroaryl, and wherein R2 is substituted with 0, 1, 2, 3, or 4 independently selected R5 groups;
- wherein each of R3a and R3b, when present, is independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 cycloalkyl, 4-10 membered heterocycloalkyl, C6-C10 aryl, —(C1-C3 alkyl)(C6-C10 aryl), and 4-10 membered heteroaryl, and wherein each of R3a and R3b is independently substituted with 0, 1, 2, 3, or 4 independently selected R5 groups;
- wherein R4 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C10 cycloalkyl, 4-10 membered heterocycloalkyl, C6-C10 aryl, and 4-10 membered heteroaryl, and —(C1-C3 alkyl)(C6-C10 aryl), and wherein R4 is substituted with 0, 1, 2, 3, or 4 independently selected R5 groups;
- wherein each occurrence of R5, when present, is independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C3 hydroxyalkyl, C1-C3 haloalkoxy, C1-C3 alkoxy, C1-C3 thioalkyl, C1-C3 alkyl(C1-C3 alkoxy), C1-C3 alkylamino, (C1-C3)(C1-C3) dialkylamino, C3-C7 cycloalkyl, C6-C10 aryl, —(C═O)(C1-C3 alkyl), —(S═O)(C1-C3 alkyl), —SO2(C1-C3 alkyl), —CO2R11, —(C═O)NR12aR12b, —SO2NR12aR12b, —O(C═O)NR12aR12b, —NHSO2NR12aR12b, and —NH(C═O)NR12aR12b;
- wherein each occurrence of R11, when present, is independently selected from hydrogen and C1-C4 alkyl;
- and
- wherein each occurrence of R12a and R12b, when present, is independently selected from hydrogen and C1-C3 alkyl.
12 more elements
Dependencies are inferred from the claim text.