Mayr's Database of Reactivity Parameters

lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles » Allyl Element Compounds » Allyl-B

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Name lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)
Structure
image of molecule
Molecule class Nucleophiles » C-Nucleophiles » Allyl Element Compounds » Allyl-B
SMILES C=CC[B-]1(OC(C)(C)C(C)(C)O1)C2=CC=CC=C2.[Li+]
Molecular formula C15H22BLiO2
Quality *
Parameters

N  Param.: 11.20

sN Param.: 0.64
Comment

This boronate complex was unstable in MeCN solutions, leading to decomposition during the course of the
measurements when conducted at higher concentrations (>2.0 x 10−3 M). Kinetics studied within the range of
boronate concentrations 4.0 x 10−4 M to 3.2 x 10−3 M were found to have second-order rate constants within 6%
error. However, the reduced rate of reaction with
benzhydrylium ion (dma)2CH+ leads to greater decomposition of this boronate compleax and a significant error in measurement. Consequently, the nucleophilicity parameter N reported has a large error (approximately ± 0.6
units).
Solvent MeCN
Reference J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240