Issue 10, 2017

Asymmetric SN2′-type C–H functionalization of arenes with propargylic alcohols

Abstract

Herein we present the first example of transition metal-mediated stereodefined β-OH elimination, an atom economical [Cp*RhCl2]2-catalyzed SN2′-type coupling between easily available arenes and non-terminal tertiary 2-alkynylic alcohols at rt affording fully substituted allenes with H2O as the only by-product. When optically active propargylic alcohols were used, asymmetric allenylation was realized with perfect chirality transfer. It is unveiled that the reversed regioselectivity for the C–C triple bond insertion is induced by the steric effect of the tertiary carbon center as well as the weak coordination nature of the hydroxyl oxygen with Rh, which is also responsible for the stereospecificity of the rather uncommon β-OH elimination forming allenes.

Graphical abstract: Asymmetric SN2′-type C–H functionalization of arenes with propargylic alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
16 7 2017
Accepted
14 8 2017
First published
15 8 2017

Org. Chem. Front., 2017,4, 2002-2007

Asymmetric SN2′-type C–H functionalization of arenes with propargylic alcohols

S. Wu, X. Huang, C. Fu and S. Ma, Org. Chem. Front., 2017, 4, 2002 DOI: 10.1039/C7QO00588A

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