TY - JOUR
T1 - Triol-promoted activation of C-F bonds
T2 - Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl) propane
AU - Champagne, Pier Alexandre
AU - Saint-Martin, Alexandre
AU - Drouin, Mélina
AU - Paquin, Jean François
PY - 2013/11/13
Y1 - 2013/11/13
N2 - Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bonddonating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bondaccepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.
AB - Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bonddonating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bondaccepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.
KW - C-F bond activation
KW - Highly concentrated conditions
KW - Hydrogen bond
KW - Nucleophilic substitution
KW - Organofluorine
KW - Triol
UR - http://www.scopus.com/inward/record.url?scp=84888615913&partnerID=8YFLogxK
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U2 - 10.3762/bjoc.9.283
DO - 10.3762/bjoc.9.283
M3 - Article
AN - SCOPUS:84888615913
SN - 1860-5397
VL - 9
SP - 2451
EP - 2456
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
ER -