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US 2026/0001830 A1Published application
Process for pd(ii)-catalyzed site-selective beta- and gamma-c(sp3)-h arylation of primary aldehydes controlled by transient directing groups
AssigneeThe Scripps Research Institute
InventorsJin-Quan Yu, Yi-Hao Li
Life of this patent
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Abstract
The present invention provides a process for Pd(II)-catalyzed site selective β- and γC(sp3)-II arylation of primary aldehydes controlled by transient directing groups.
Claims41
A process for preparing a compound of Formula (I)
- wherein:
- R is C1-C10 alkyl that is optionally substituted with one substituent selected from the group consisting of C3-C7 cycloalkyl, C6-C10 aryl, halo, —O—C(═O)-(C1-C6 alkyl), —O-(C6-C10 aryl), and —O-(C1-C6 alkyl) wherein the C1-C6 alkyl of the —O-(C1-C6 alkyl) is optionally substituted with C6-C10 aryl;
- C3-C7 cycloalkyl;
- and C6-C10 aryl;
- R1 is hydrogen, halo, —C(═O)-(C1-C6 alkyl), halo(C1-C6 alkyl), C1-C6 alkyl, —NO2, —C(═O)—OH, —CN, —C(═O)—O-(C1-C6 alkyl), and —O-(C1-C6 alkyl), or 13 O-halo(C1-C6 alkyl);
- comprising reacting a compound of Formula (II)
- wherein R in Formula (II) is as defined above for Formula (I);
- with a compound of Formula (III)
- wherein R1 in Formula (III) is as defined above for Formula (I);
- in the presence of a palladium salt, an amino acid based transient directing group compound (TDG), a 2-pyridone ligand (L), a salt composition comprising at least one silver salt, and an acid composition comprising acetic acid or an acetic acid derivative.
7 more elements
A process for preparing a compound of Formula (IV)
- wherein:
- R2 is H, or C1-C6 alkyl;
- R3 is C3-C7 cycloalkyl;
- or C1-C6 alkyl which is optionally substituted with a substituent selected from the group consisting of —O—C(═O)-C1-C6 alkyl and C6-C10 aryl;
- and
- R4 is selected from the group consisting of —C(═O)-(C1-C6 alkyl);
- —C(═O)—O-(C1-C6 alkyl);
- —C(═O)—O -(C3-C10 bicyclic carbocyclyl) wherein said C3-C10 bicyclic carbocyclyl is optionally substituted with C1-C6 alkyl;
- halo;
- halo (C1-C6 alkyl);
- —NO2;
- —CN;
- comprising reacting a compound of Formula (V)
- wherein R2 and R3 in Formula (V) are as defined above for Formula (IV);
- with a compound of Formula (VI)
- wherein R4 in Formula (VI) is as defined above for Formula (IV);
- in the presence of a palladium salt, an amino acid based transient directing group compound (TDG), a 2-pyridone ligand (L), a salt composition comprising at least one silver salt, and an acid composition comprising acetic acid or an acetic acid derivative.
14 more elements
A process for preparing a compound of Formula (VII)
- wherein:
- R5 and R6 together with the carbon atoms to which they are shown attached form a C4-C7 cycloalkyl;
- and
- R7 is selected from the group consisting of —C(═O)-(C1-C6 alkyl);
- —C(═O)—O-(C1-C6 alkyl);
- —C(═O)—O-(C3-C10 bicyclic carbocyclyl) wherein said C3-C10 bicyclic carbocyclyl is optionally substituted with C1-C6 alkyl;
- halo;
- halo (C1-C6 alkyl);
- —NO2;
- —CN;
- comprising reacting a compound of Formula (VIII)
- wherein R5 and R6 are as defined above for Formula (VII);
- with a compound of Formula (IX)
- wherein R7 is as defined above for Formula (VII);
- in the presence of a palladium salt, an amino acid based transient directing group compound (TDG), a 2-pyridone ligand (L), a salt composition comprising at least one silver salt, and an acid composition comprising acetic acid or an acetic acid derivative.
12 more elements
Dependencies are inferred from the claim text.