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Transition metal and radical free 1,2-dicarbofunctionalisation of 1,1-arylboryl alkenes through dual C(sp3)-C(sp3) bond formation

17 January 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We reveal here the regioselective nucleophilic addition of C(sp3) to 1,1-arylboryl alkenes, followed by nucleophilic attack of the alpha-boryl carbanionic intermediates to C(sp3) electrophiles, at room temperature. We envisioned this goal through engaged C(sp3) chemical entities avoiding metal catalysts, additives, radical initiators or specific irradiation. This multicomponent reaction guarantees that the new tetrasubstituted carbon formed retains all the C atoms from the three starting materials involved in the assembly.

Keywords

multicoponent reactions
dicarbofunctionalisation
assembly
tetrasubstituted carbon
enantioselectivity

Supplementary materials

Title
Description
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Title
Supporting Information
Description
General Information General methodology for 1,2-dialkylation General methodology for alkylation/protonation General methodology for cyclopropanation General methodology for transborylation of alkenylboranes Characterization of tertiary boronic esters Characterization of secondary boronic esters Characterization of silylpinacolborylcyclopropanes Characterization of tertiary and secondary alcohols NMR Spectra Enantiomeric Excess determined by HPLC 11B NMR spectroscopic studies
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Version History

Jan 17, 2022 Version 1

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The content is available under CC BY NC 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-vrsfr
D O I: 10.26434/chemrxiv-2022-vrsfr [opens in a new tab]

Funding

Ministerio de Economía y Competitividad
PID2019-109674GB-I00

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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