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Dirhodium(II)‐Catalyzed C(sp 2 )−H Azidation of Benzaldehydes
Author(s) -
Wang Yi,
Fang Zaixiang,
Chen Xiaochuan,
Wang Yuanhua
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905855
Subject(s) - regioselectivity , chemistry , electrophile , aldehyde , azide , catalysis , aryl , electrophilic aromatic substitution , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
Multiple steps are needed to achieve the C−H functional of aromatic aldehyde, since the C−H functional reaction usually occurs preferentially at the aldehydic C−H bond over the aryl C−H bond. We report an efficient azidation method mediated by dirhodium(II) catalysts to achieve the direct aryl azidation of aromatic aldehydes avoiding the simultaneous use of protected aldehydes and prefunctionalized arenes. The regioselectivity of this method is similar to those of typical aromatic electrophilic substitution reactions. The resulting azidobenzaldehyde products are versatile building blocks or precursors for the synthesis of many biologically active compounds. The mechanism studies indicate that the one‐electron oxidative intermediate Rh 2 (II,III) N 3 is responsible for the azide transfer.