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Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf) 3 ‐Catalyzed Friedel–Crafts‐Type Benzylation
Author(s) -
Yurino Taiga,
Hachiya Asuka,
Suzuki Keisuke,
Ohkuma Takeshi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000077
Subject(s) - friedel–crafts reaction , chemistry , chemoselectivity , catalysis , electrophile , yield (engineering) , phosphate , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , materials science , metallurgy
Al(OTf) 3 was identified as a high‐performance catalyst for Friedel–Crafts‐type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol‐% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.