Transfer Vinylation and Dienylation via Rhodium(I)-Catalyzed Deketonation of Allylic Alcohols

The C–O and C–H bond cleavages of simple allylic alcohols have witnessed tremendous progress in recent years. However, an efficient method for cleaving the C–C bond via β-carbon elimination is still comparatively underexploited. In this study, we demonstrate rhodium­(I)-catalyzed deketonative transf...

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Published inACS catalysis Vol. 12; no. 12; pp. 7030 - 7036
Main Authors Liu, Zheng-Qiang, Liang, Cheng, Luo, Zhen, Wu, Yu-Fei, Hong, Chuan-Ming, Li, Qing-Hua, Liu, Tang-Lin
Format Journal Article
LanguageEnglish
Published American Chemical Society 17.06.2022
Subjects
tertiary allylic alcohols
transfer vinylation and dienylation
C−C bond activation
rhodium-catalyzed
β-vinyl and β-dienyl elimination
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Summary:The C–O and C–H bond cleavages of simple allylic alcohols have witnessed tremendous progress in recent years. However, an efficient method for cleaving the C–C bond via β-carbon elimination is still comparatively underexploited. In this study, we demonstrate rhodium­(I)-catalyzed deketonative transfer vinylation and transfer dienylation of various tertiary allylic alcohols with ketones via β-vinyl and β-dienyl elimination. Under mild reaction conditions, allylic and dienyl alcohols with quaternary centers were thus selectively and efficiently constructed in moderate to good yields. The methodologies of transfer vinylation and transfer dienylation, which would provide access to a range of useful organic compounds, pave a significant way for transition-metal-catalyzed C–C activation in organic synthesis.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c02325