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Organic & Biomolecular Chemistry
Page 4 of 6
DOI: 10.1039/C7OB00040E
COMMUNICATION
Journal Name
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properties were submitted to standard conditions with several
benzox/benzimidazolinones (Table 5). All reactions proceed
smoothly to give moderate yields, and the regioselectivities
were in line with that previously observed in Table 3 with one
exception. The coupling of 6i with 5h gave an inseparable o/m
regio-mixture of 7o in 3/1 ratio which was deviated from the
1.1/1 ratio of o/m 2p (entry 5 vs Table 3 entry 7). This
inconsistency in regioselectivity may reflect the greater
bulkiness of N-nucleophile of 6i than that of S-nucleophile of
1b
.
In summary, with o-silyl aryltriflate as aryne precursor,
methodology for selective arylation of 2-oxazolidinethione and
2-benzoxazolinethione at the sulfur atom rather than the
nitrogen atom to give 2-(arylthio)oxazole and 2-
(phenylthio)benzoxazole has been developed; meanwhile, for
the reaction of 2-benzoxazolinone and 2-benzimidazolinone,
the arylation occurs solely at the nitrogen atom instead of
oxygen atom affording N-aryl benzoxazolone and N-aryl
benzimidazolinone respectively. The mild reaction conditions
and simple operations of the current protocol provide an
efficient and convenient access toward biologically important
aryl sulfide and aryl amine derivatives.
Acknowledgements
The authors wish to thank the Natural Science Foundation of
(5)
China (21272077,21402014 and 21672027), QingLan Project
of Jiangsu Province (2016) and Six-Talent-Peaks Program of
Jiangsu (2017) for financial support.
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