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Title: Redox-enabled direct stereoconvergent heteroarylation of simple alcohols
Authors: Liu, Yongbing 
Tao, Ran
Lin, Zhi-Keng
Yang, Guoqiang 
Zhao, Yu 
Issue Date: 19-Aug-2021
Publisher: Nature Research
Citation: Liu, Yongbing, Tao, Ran, Lin, Zhi-Keng, Yang, Guoqiang, Zhao, Yu (2021-08-19). Redox-enabled direct stereoconvergent heteroarylation of simple alcohols. Nature Communications 12 (1) : 5035. ScholarBank@NUS Repository.
Rights: Attribution 4.0 International
Abstract: The direct transformation of racemic feedstock materials to valuable enantiopure compounds is of significant importance for sustainable chemical synthesis. Toward this goal, the radical mechanism has proven uniquely effective in stereoconvergent carbon-carbon bond forming reactions. Here we report a mechanistically distinct redox-enabled strategy for an efficient enantioconvergent coupling of pyrroles with simple racemic secondary alcohols. In such processes, chirality is removed from the substrate via dehydrogenation and reinstalled in the catalytic reduction of a key stabilized cationic intermediate. This strategy provides significant advantage of utilizing simple pyrroles to react with feedstock alcohols without the need for leaving group incorporation. This overall redox-neutral transformation is also highly economical with no additional reagent nor waste generation other than water. In our studies, oxime-derived iridacycle complexes are introduced, which cooperate with a chiral phosphoric acid to enable heteroarylation of alcohols, accessing a wide range of valuable substituted pyrroles in high yield and enantioselectivity. © 2021, The Author(s).
Source Title: Nature Communications
ISSN: 2041-1723
DOI: 10.1038/s41467-021-25268-1
Rights: Attribution 4.0 International
Appears in Collections:Staff Publications

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