Journal
ORGANIC LETTERS
Volume 24, Issue 32, Pages 5951-5956Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02210
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Funding
- National Natural Science Foundation of China [91753126, 21622207]
- CAS Interdisciplinary Innovation Team [JCTD-2020-16]
- Program of Shanghai Academic/Technology Research Leader [21XD1424700]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20020200]
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In this study, a method for synthesizing various delta-alkynols through delta-C-H alkynylation is reported. The key intermediate, a hypervalent iodine-coordinated benziodoxole-alkoxyl-iminophenylacetic acid complex, was characterized by X-ray crystallography for the first time. The reaction is compatible with sensitive functional groups and exhibits excellent regioselectivity for the synthesis of delta-alkynols with diverse substituents. Furthermore, the method can be extended to the synthesis of delta-hydroxylalkenes and delta-hydroxylnitriles, and the resulting delta-alkynol products can be easily derivatized to other valuable bifunctional building blocks.
Here we report (delta-C-H alkynylation to synthesize various (delta-alkynols from iminophenylacetic acids. The hypervalent iodine-coordinated benziodoxole-alkoxyl-iminophenylacetic acid complex was the key intermediate and was characterized by X-ray crystallography for the first time. (delta-C-H alkynylation is compatible with sensitive functional groups, including azides, aldehydes, and free alcohols, for the synthesis of (delta-alkynols with diversified substituents in excellent regioselectivity. This reaction extends to (delta-hydroxylalkene and (delta-hydroxylnitrile synthesis, and the (delta-alkynol products are easily derivatized to other valuable bifunctional building blocks.
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