Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

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

Title
Description
Actions
Title
SI - Experimental Section and Notes
Description
Actions
Title
SI - NMR Spectra
Description
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

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

Metrics

4,950
1,316
0
Views
Downloads
Citations

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
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

Share