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Exploring Multistep Continuous‐Flow Hydrosilylation Reactions Catalyzed by Tris(pentafluorophenyl)borane
Author(s) -
Wilkins Lewis C.,
Howard Joseph L.,
Burger Stefan,
FrentzelBeyme Louis,
Browne Duncan L.,
Melen Rebecca L.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700349
Subject(s) - chemistry , hydrosilylation , flow chemistry , borane , continuous flow , reactivity (psychology) , aldehyde , hydroamination , catalysis , aniline , tris , lewis acids and bases , frustrated lewis pair , boron , imine , combinatorial chemistry , organic chemistry , polymer chemistry , biochemistry , physics , mechanics , medicine , alternative medicine , pathology
Exploring the combination of continuous‐flow processes with the boron Lewis acid catalyzed hydrosilylation of aldehydes and ketones has delivered a robust and generally applicable reaction protocol. Notably this approach permits ready access to high temperatures and pressures and thus allows improved reactivity of substrates that were previously recalcitrant under the traditional approach. Efforts to quench the output from the flow reactor with water showed surprising tolerance leading to the application of continuous‐flow systems in multistep imine formation/hydrosilylation processes to generate the corresponding secondary amines from their aldehyde and aniline precursors.