13397-98-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 845, 1980 DOI: 10.1016/S0040-4039(00)71521-8

Upstream product

• 104-51-8 1-butylbenzene 
• 599-91-7 propyl tosylate 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 693-03-8 n-butyl magnesium bromide 
• 583-53-9 2,3-dibromobenzene 
• 71813-50-8 1-bromo-2-(but-3-enyl)benzene 

Downstream Products

• 1438826-22-2 C₁₈H₃₁BO₂Si 
• 1438827-34-9 4,4,5,5-tetramethyl-2-(1-phenylbutyl)-1,3,2-dioxaborolane 
• 1438827-46-3 C₁₆H₂₄⁽²⁾HBO₂ 
• 1438827-52-1 C₁₆H₂₄BIO₂ 
• 177950-00-4 C₁₇H₂₇BO₂ 
• 1438827-73-6 1-methoxy-4-(1-phenylbutyl)benzene 
• 839-96-3 1-methoxy-3-(1-phenylbutyl)benzene 
• 1438824-66-8 (2-butylphenyl)dimethylsilane 
• 1520-44-1 1,3-diphenylbutane 
• 114160-94-0 <2-n-Butyl-benzhydryl>-<2-dimethylamino-aethyl>-aether 
• 101596-04-7 2-Butyl-benzhydrylchlorid 
• 4973-08-4 2-Butyl-1-(2-butyl-phenyl)-cyclohexan-1-ol 
• 107923-32-0 2-Butyl-benzhydrol 

Relevant academic research and scientific papers

Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane

Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

Bromination of alkylbenzenes in organic solvents. Substrate and position selectivity and effects of substituents

The relative reactivity and the orientation of the entering group in the reaction of bromine with alkylbenzenes (C1-C4 alkyl groups, the last two with normal and iso structures) in organic solvents (acetic acid, acetic anhydride, nitromethane) under polythermal conditions (25-75 deg C) are determined mainly by the steric effects of the substituents.Nathan-Baker position and substrate effects are observed.Correlations close to linear are observed between the orientation (in the form of log 2P/O, where P and O are the relative amounts of the isomers in their reaction mixture) and the purely steric constants of the alkyl groups Es0.The substrate selectivity depends nonlinearly and inversely on Es0.The sensitivity of the orientation to change in the steric characteristics of the substituents shows an extremal dependence on the temperature with a maximum at about 50 deg C.

SELECTIVE MONO-ALKYLATION AND ARYLATION OF AROMATIC DIHALIDES BY PALLADIUM-CATALYZED CROSS-COUPLING WITH THE GRIGNARD AND ORGANOZINC REAGENTS

Dibromobenzene, dibromothiophenes, dichloro- and dibromopyridine are highly selectively mono-alkylated and arylated with Grignard or organozinc reagents in the presence of palladium complexes as catalysts.