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Issue 93, 2020
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Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

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Abstract

The first stereoconvergent Suzuki–Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides.

Graphical abstract: Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

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Article information


Submitted
22 Jul 2020
Accepted
14 Oct 2020
First published
28 Oct 2020

Chem. Commun., 2020,56, 14661-14664
Article type
Communication

Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

C. C. Tyrol, N. S. Yone, C. F. Gallin and J. A. Byers, Chem. Commun., 2020, 56, 14661
DOI: 10.1039/D0CC05003B

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