Alcohol-alcohol cross-coupling enabled by S H 2 radical sorting

Alcohols represent a functional group class with unparalleled abundance and structural diversity. In an era of chemical synthesis that prioritizes reducing time to target and maximizing exploration of chemical space, harnessing these building blocks for carbon-carbon bond-forming reactions is a key...

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Published inScience (American Association for the Advancement of Science) Vol. 383; no. 6689; pp. 1350 - 1357
Main Authors Chen, Ruizhe, Intermaggio, Nicholas E, Xie, Jiaxin, Rossi-Ashton, James A, Gould, Colin A, Martin, Robert T, Alcázar, Jesús, MacMillan, David W C
Format Journal Article
LanguageEnglish
Published United States 22.03.2024
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Summary:Alcohols represent a functional group class with unparalleled abundance and structural diversity. In an era of chemical synthesis that prioritizes reducing time to target and maximizing exploration of chemical space, harnessing these building blocks for carbon-carbon bond-forming reactions is a key goal in organic chemistry. In particular, leveraging a single activation mode to form a new C(sp )-C(sp ) bond from two alcohol subunits would enable access to an extraordinary level of structural diversity. In this work, we report a nickel radical sorting-mediated cross-alcohol coupling wherein two alcohol fragments are deoxygenated and coupled in one reaction vessel, open to air.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.adl5890