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US 11,918,984 B2Granted
Annulation catalysts via direct C—H bond amination
AssigneePresident and Fellows of Harvard College
InventorsTheodore Alexander Betley, Alexandre Mikhailine, Claudia Kleinlein, Yuyang Dong, Yunjung Baek
Life of this patent
Estimating the term…
Abstract
Disclosed are compounds, methods, reagents, systems, and kits for the preparation and utilization of monomeric or polymeric metal-based compounds. These metal-based compounds are organometallic catalysts composed of substituted dipyrrin ligands bound to transition metals. C—H bond functionalization catalysis can be performed with the disclosed organometallic catalysts to yield C—N bonds to generate substituted bicyclic, spiro, and fused nitrogen-containing heterocycles, all common motifs in various pharmaceutical and bioactive molecules.
Claims20
A compound of Formula (I):
- or a salt thereof,
- wherein:
- each R1 independently is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- A is substituted or unsubstituted arylene;
- or substituted or unsubstituted heteroarylene;
- L is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- or
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- X is S, O, or NRX, wherein RX is hydrogen;
- nitrogen protecting group;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted arylene;
- or substituted or unsubstituted heteroarylene;
- M is a transition metal;
- and
- n is an integer between 2 and 10, inclusive;
- wherein the atom X labeled “*” of one monomer is bonded to the transition metal M labeled “**” of another monomer.
18 more elements
A compound of Formula (I-a):
- or a salt thereof,
- wherein:
- each R1 independently is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- A is substituted or unsubstituted arylene;
- or substituted or unsubstituted heteroarylene;
- L is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- or branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- and
- X is S, O, or NRX, wherein RX is hydrogen;
- nitrogen protecting group;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted arylene;
- or substituted or unsubstituted heteroarylene.
14 more elements
A compound of Formula (II):
- or a salt thereof,
- wherein:
- each R3 independently is hydrogen;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- substituted or unsubstituted heteroaryl;
- —SRX or —ORX, wherein RX is hydrogen;
- oxygen protecting group;
- sulfur protecting group;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- or —N(RX)2, wherein each RX independently is hydrogen;
- nitrogen protecting group;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- A is substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- each B independently is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- X1 is a substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- or substituted or unsubstituted heteroarylene;
- and
- M is a transition metal.
27 more elements
A compound of Formula (III):
- or a salt thereof,
- wherein:
- A is substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- each B independently is branched or unbranched, substituted or unsubstituted, cyclic or acyclic aliphatic;
- branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- X2 is branched or unbranched, substituted or unsubstituted, cyclic or acyclic heteroaliphatic;
- substituted or unsubstituted aryl;
- or substituted or unsubstituted heteroaryl;
- . . . is a bond or absent;
- and
- M is a transition metal.
11 more elements
Dependencies are inferred from the claim text.