Beilstein J. Org. Chem. 2018, 14, 1016–1020.
ORCID® iDs
in chloroform solution under reflux conditions afforded the
desired product 11a in good yield. As expected, the reactions of
benzoic acid (9b) with benzyl alcohol (10a) or 1-pentanol (10b)
under the same conditions gave the corresponding esters 11b or
11c in moderate yields (Scheme 3, reaction 1). The analogous
reaction of butyric acid (9a) with benzylamine (12) and benz-
iodazole 7a under similar conditions produced the expected
amide 13 in moderate yield (Scheme 3, reaction 2). Compared
to the iodosodilactone reagents 3 [23-25], benziodazole 7a
showed a comparable or better reactivity. In contrast to
iodosodilactone, benziodazole 7a has excellent solubility in
chloroform allowing reactions in solution under homogeneous
conditions. Similar to the reactions of iodosodilactone 3,
Ph3P=O and amide 6a were observed as the byproducts in these
reactions (Scheme 3), which is in agreement with the previ-
ously proposed mechanism of oxidatively assisted esterifica-
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Acknowledgements
This work was supported by a research grant from the Russian
Science Foundation (RSF-16-13-10081). A.S. is also thankful to
JSPS Grant-in-Aid for Scientific Research (C, Grant No
15K07852) and to the JSPS Fund for the Promotion of Joint
International Research (Grant No 16KK0199). V.V.Z. is
thankful for support from the Office of the Vice President for
Research, University of Minnesota.
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