Mild Condition for the Deoxygenation of α‑Heteroaryl-Substituted Methanol Derivatives

A mild condition via PPh3/I2/imidazole for the deoxygenation of substituted methanol derivatives has been identified. This metal-free process was found to proceed well on secondary or tertiary alcohols substituted with one or two heteroaryl groups, and it tolerates acid-sensitive heterocycles. This...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 86; no. 8; pp. 5560 - 5567
Main Authors:	Meng, Na, Yu, Wensheng, Suzuki, Takao, Chen, Maofen, Qi, Zhiqi, Hu, Bin, Bao, Jianming, Debenham, John S, Mazzola, Robert, Duffy, Joseph L
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 16-04-2021
Online Access:	Get full text
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Summary:	A mild condition via PPh3/I2/imidazole for the deoxygenation of substituted methanol derivatives has been identified. This metal-free process was found to proceed well on secondary or tertiary alcohols substituted with one or two heteroaryl groups, and it tolerates acid-sensitive heterocycles. This condition works for methanol derivatives substituted with 2-pyridyl, 4-pyridyl, or other heterocyclic groups, allowing the negative charge formed during the reaction to resonate to a nitrogen atom. Methanol derivatives substituted with 3-pyridyl or heterocyclic groups that do not allow the negative charge formed during the reaction to resonate to a nitrogen atom will not undergo deoxygenation under this condition.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.1c00067