Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades

Stereochemical control of acyclic carbon radical intermediates remains a challenge, due to the difficulty in differentiation between the two faces of the planar species. Here the authors show diastereodivergent hydrogen atom transfer to acyclic carbon radicals via control of N-heterocyclic carbene–b...

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Main Authors: Tian Ye, Feng-Lian Zhang, Hui-Min Xia, Xi Zhou, Zhi-Xiang Yu, Yi-Feng Wang
Format: Article
Language:English
Published: Nature Portfolio 2022-01-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/s41467-022-28071-8
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author Tian Ye
Feng-Lian Zhang
Hui-Min Xia
Xi Zhou
Zhi-Xiang Yu
Yi-Feng Wang
author_facet Tian Ye
Feng-Lian Zhang
Hui-Min Xia
Xi Zhou
Zhi-Xiang Yu
Yi-Feng Wang
author_sort Tian Ye
collection DOAJ
description Stereochemical control of acyclic carbon radical intermediates remains a challenge, due to the difficulty in differentiation between the two faces of the planar species. Here the authors show diastereodivergent hydrogen atom transfer to acyclic carbon radicals via control of N-heterocyclic carbene–borane reagents with either a thiol catalyst or a Lewis acid.
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spelling doaj.art-b7add9506ee644c2af1e4b561f00c1092022-12-21T23:43:16ZengNature PortfolioNature Communications2041-17232022-01-0113111210.1038/s41467-022-28071-8Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascadesTian Ye0Feng-Lian Zhang1Hui-Min Xia2Xi Zhou3Zhi-Xiang Yu4Yi-Feng Wang5Department of Chemistry, University of Science and Technology of ChinaDepartment of Chemistry, University of Science and Technology of ChinaDepartment of Chemistry, University of Science and Technology of ChinaDepartment of Chemistry, University of Science and Technology of ChinaBeijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking UniversityDepartment of Chemistry, University of Science and Technology of ChinaStereochemical control of acyclic carbon radical intermediates remains a challenge, due to the difficulty in differentiation between the two faces of the planar species. Here the authors show diastereodivergent hydrogen atom transfer to acyclic carbon radicals via control of N-heterocyclic carbene–borane reagents with either a thiol catalyst or a Lewis acid.https://doi.org/10.1038/s41467-022-28071-8
spellingShingle Tian Ye
Feng-Lian Zhang
Hui-Min Xia
Xi Zhou
Zhi-Xiang Yu
Yi-Feng Wang
Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
Nature Communications
title Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
title_full Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
title_fullStr Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
title_full_unstemmed Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
title_short Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades
title_sort stereoselective hydrogen atom transfer to acyclic radicals a switch enabling diastereodivergent borylative radical cascades
url https://doi.org/10.1038/s41467-022-28071-8
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