Journal
ORGANIC LETTERS
Volume 22, Issue 4, Pages 1239-1243Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04185
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Funding
- National Natural Science Foundation of China [21572162]
- Natural Science Foundation of Zhejiang Province [LY20B020015, LQ18B020006]
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The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)-chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.
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