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Palladium‐Catalyzed Regioselective Dehydrogenative C–H/C–H Cross‐Coupling of Pyrroles and Pyridine N ‐Oxides
Author(s) -
Liu Shanshan,
Tzschucke C. Christoph
Publication year - 2016
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.201600680
Subject(s) - chemistry , hydrogenolysis , palladium , catalysis , regioselectivity , pyridine , medicinal chemistry , pyrrole , stoichiometry , hydrolysis , organic chemistry
The palladium‐catalyzed cross‐dehydrogenative coupling of N ‐alkylpyrroles and pyridine N ‐oxides gave the corresponding pyrrolylpyridine N ‐oxides. Cu(OAc) 2 · H 2 O as a co‐catalyst with air as the terminal oxidant led to preferential coupling in the β‐position, whereas AgOAc as the stoichiometric oxidant resulted in preferential coupling in the α‐position. N ‐(Benzyloxymethyl)pyrrole derivatives were deprotected by hydrogenolysis followed by basic hydrolysis.