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Hydroalkylation of Olefins to form Quaternary Carbons

15 March 2019, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Metal-hydride hydrogen atom transfer (MHAT) functionalizes unbiased alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that allows for the hydroalkylation of unactivated olefins by unactivated alkyl halides, yielding aliphatic quaternary carbons.

Keywords

Branched-Selective
Hydrogen Atom Transfer
Nickel Catalysis
Manganese Catalysis
Quaternary Carbons
Hydroalkylation

Supplementary materials

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Description
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SI - Experimental Section and Notes
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SI - NMR Spectra
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Now Published

Hydroalkylation of Olefins To Form Quaternary Carbons [opens in a new tab]
Samantha A. Green, Tucker R. Huffman, Ruairí O. McCourt, Vincent van der Puyl, Ryan A. Shenvi journal article
Journal of the American Chemical Society , Volume 141, Issue 19
Online publication date: Apr 29, 2019

Version History

Mar 15, 2019 Version 1

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

DOI

10.26434/chemrxiv.7848446.v1
D O I: 10.26434/chemrxiv.7848446.v1 [opens in a new tab]

Funding

R35 GM122606
NSF GRFP

Author’s competing interest statement

No conflict of interest

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