Methods for synthesizing vinylidenes and alkenes
Inventors
Bara, Jason Edward • O'Harra, Kathryn Elizabeth
Assignees
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Publication Number
US-11572355-B2
Publication Date
2023-02-07
Expiration Date
Abstract
The present disclosure provide synthetic methods for the synthesis of N-substituted vinylidene and alkene compounds in addition to compounds formed from such methods.
Core Innovation
The invention relates to a method for synthesizing a compound of Formula VI by reacting a compound of Formula II with a compound of Formula VII, or with an acetal derivative or a polyacetal derivative thereof, at elevated temperature to form the compound of Formula VI. The overall description also includes converting symmetric carbonyl/carbamoyl precursors with paraformaldehyde or other aldehyde, acetal, or polyacetal derivatives to form vinylidene products of Formula I and Formula VI.
Cationic vinylidene compounds are provided as compounds of Formula III or Formula III-a, each being balanced by one or more anions. The anions are selected from halides and other anion types, including hydroxide, bis(trifluoromethanesulfonyl)amide (NTf2), hexafluorophosphate (PF6), triflate, dicyanamide, tetrafluoroborate (BF4), thiocyanate, and nitrate.
The substituent framework allows variation of R1, R2, R3, R4/R5, R6/R7, R10, R11, and R20, each optionally substituted with one or more Z groups. R4 and R5, and similarly R6 and R7, may be independently selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, or brought together with the nitrogen to which they are attached to form a heterocycle ring or a heteroaryl ring, optionally substituted with one or more Z groups. The vinylidene compounds are used to form polymers comprising monomeric units of Formula V, V-a, and V-b, together with anions associated with the cationic units.
Claims Coverage
The patent identifies independent claims directed to a method for synthesizing a compound of Formula VI and to charge-balanced vinylidene compounds of Formula III or Formula III-a. Across these claims, the inventive features center on the elevated-temperature reaction, the broad substituent framework controlled by R and Z definitions, the anion-balanced cationic vinylidene compounds, and the use of the compounds in polymer formation.
Elevated-temperature condensation to form Formula VI from Formula II and Formula VII or acetal or polyacetal derivatives
A method for synthesizing a compound of Formula VI by reacting a compound of Formula II with a compound of Formula VII or an acetal derivative or a polyacetal derivative thereof at elevated temperature to form the compound of Formula VI.
Broad substitution framework with optional Z substituents
R1 is selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, heteroaryl, OR3, SR3, and NR4R5, where each may be optionally substituted with one or more Z groups; R2 is NR6R7; R3 is selected from alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each optionally substituted with one or more Z groups; R4 and R5 are independently selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each optionally substituted with one or more Z groups; and R6 and R7 are independently selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each optionally substituted with one or more Z groups; with R20 selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each optionally substituted with one or more Z groups.
N-attached heterocycle or heteroaryl ring formation from R4/R5 and from R6/R7
R4 and R5 may be brought together with the nitrogen to which they are attached to form a heterocycle ring or a heteroaryl ring, optionally substituted with one or more Z groups; and R6 and R7 may be brought together with the nitrogen to which they are attached to form a heterocycle ring or a heteroaryl ring, optionally substituted with one or more Z groups.
Charge-balanced vinylidene compounds of Formula III or Formula III-a
A compound of Formula III or Formula III-a and one or more anions balancing the charge of the compound of Formula III or Formula III-a.
Defined substituent and atom selection constraints
R10 and R11 independently selected from alkyl, cycloalkyl, aryl, or heteroaryl, optionally substituted with one or more Z groups; X1, X2, X3, X4, X5, and X6 independently selected from N, C–H, or C–Z with the constraints that no more than one of X1, X2, and X3 are N and no more than one of X4, X5, and X6 are N; R20 selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, optionally substituted with one or more Z groups; and Z independently selected at each occurrence from the listed set.
Depicted variant selection
The compound is selected from the depicted set of variants, including variants with specific counterions/labels.
Overall claim coverage centers on a method for producing a Formula VI compound by reacting Formula II with Formula VII or acetal or polyacetal derivatives at elevated temperature, and on charge-balanced vinylidene compounds of Formula III or Formula III-a with constrained substituent and atom selection. The claims further define extensive Z-substituted scope, optional heterocycle or heteroaryl ring formation from N-attached substituents, and dependent selection of depicted variants.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Polymer synthesis providing polymers comprising monomeric units of Formula V, V-a, and V-b, together with anions associated with the cationic units, including a representative Polymer 1 depicted in the figures.
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