Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf) 3 ‐Catalyzed Friedel–Crafts‐Type Benzylation | Zendy

Yurino Taiga | Zendy; Hachiya Asuka | Zendy; Suzuki Keisuke | Zendy; Ohkuma Takeshi | Zendy

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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.

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