CROSS-COUPLING OF UNACTIVATED SECONDARY BORONIC ACIDS

摘要

Provided are methods for site- and stereo-retentive cross-couplings with unactivated secondary boronic acids, which methods are particularly useful in building block-based approach for small molecule synthesis. Also provided is a method of forming an air-stable chiral secondary boronic acid.

主权项

1. A method of forming a product represented by R1R2CH-Ar, comprising:
combining a secondary boronic acid represented by R1R2CH—B(OH)2; an aryl halide represented by Ar-X; a Pd catalyst; a ligand; and Ag2O:wherein, independently for each occurrence,
R1 and R2 are selected from the group consisting of substituted C1-C6 alkyl and unsubstituted C1-C6 alkyl; or R1 and R2, taken together with the carbon to which they are joined, form a substituted or unsubstituted C3-C8 cycloalkyl; Ar represents a substituted or unsubstituted monocyclic or polycyclic aryl; X represents halogen; Pd catalyst represents Pd(0) or Pd(II); ligand is P(o-R-phenyl)3; and R represents C1-C4 alkyl; thereby forming a product represented by R1R2CH-Ar.