Ti-Catalyzed Dehydroxylation of Tertiary Alcohols

Herein we report a Ti-catalyzed direct dehydroxylation of tertiary aliphatic alcohols under mild reaction conditions, forging Barton-type deoxygenation products. This protocol tolerates a wide range of functional groups, including primary alkyl chloride and carbonyl groups. It allows for selective d...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 46; pp. 8459 - 8464
Main Authors Lin, Quan, Tong, Weiqi, Shu, Xing-Zhong, Chen, Yunrong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.11.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SITE-SELECTIVE DEOXYGENATION
FORMIC-ACID
TRANSFER HYDROGENOLYSIS
BENZYLIC ALCOHOLS
SECONDARY
BIO
ARYL
B(C6F5)-CATALYZED REDUCTION
CLEAVAGE
EFFICIENT
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Summary:Herein we report a Ti-catalyzed direct dehydroxylation of tertiary aliphatic alcohols under mild reaction conditions, forging Barton-type deoxygenation products. This protocol tolerates a wide range of functional groups, including primary alkyl chloride and carbonyl groups. It allows for selective dehydroxylation of tertiary alcohols in diols and the formation of deuterated products with moderate deuterium incorporation. The efficient modification of several drugs and natural products (or their derivatives) highlights the synthetic utility of this method.
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c03119