Development of a mild and versatile directed cycloaddition approach to pyridines.

Development of a mild and versatile directed cycloaddition approach to pyridines.
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DOI:
10.1002/chem.201403916
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发表时间:
2014-09-26
影响因子:
4.3
通讯作者:
Harrity, Joseph P. A.
Harrity, Joseph P. A.
中科院分区:
化学2区
文献类型:
--
作者:
Bachollet, Sylvestre P. J. T.;Vivat, Jerome F.;Cocker, Dean C.;Adams, Harry;Harrity, Joseph P. A.

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The aza-Diels–Alder cycloaddition of 1,2,4-triazines with alkynes offers a rapid and convenient method for the synthesis of highly substituted pyridines, but often requires harsh conditions and long reaction times. The present study offers a solution to these limitations by use of a temporary tether established by a Lewis acid–base complexation of in situ generated alkynylboranes and triazines bearing a Lewis basic donor. The cycloaddition reactions take place within 20 min at 40 °C and provide direct access to a broad range of pyridines with complete and predictable regiocontrol. The carbon—boron bond can be further functionalised by cross-coupling allowing further functionality to be introduced after cycloaddition.
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