Mayr's Database of Reactivity Parameters

lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate

Information panel

Name lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate
Structure
Molecule class Nucleophiles » C-Nucleophiles » Alkyl and Aryl Boron Compounds » Arylating Boron Compounds
SMILES CC(S1)=CC=C1[B-]2(C3=CC=C(N(C)C)C=C3)OC(C)(C)C(C)(C)O2.[Li+]
Molecular formula C19H27BLiNO2S
Quality **
Parameters

N  Param.: 8.02

sN Param.: 0.89
Comment unselective attack of electrophiles at the C-B bond to the thiophenyl and to the anilino ring (ca. 1:1).
Solvent MeCN
Reference Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562