Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

Tiantian Chen; Yang Yang; Liyu Xie; Haijian Yang; Guangbin Dong; Dong Xing

doi:10.26434/chemrxiv.7072646.v3

Organic Chemistry

Search within Organic Chemistry

Ni(0)-Catalyzed α-Allylic Alkylation of Regular Ketones with 1,3-Dienes under pH and Redox-neutral Conditions

15 April 2019, Version 3

Working Paper

Show author details

This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report a Ni(0)-catalyzed cross coupling reaction between simple ketones and 1,3-dienes. A variety of a-allylic alkylation products were formed in an 1,2-addition manner with excellent regioselectivity. Water was found to significantly accelerate this transformation. A HO-Ni-H species generated from oxidative addition of Ni(0) to H₂O is proposed to play a “dual role” in activating both the ketone and the diene substrate.

Keywords

Supplementary materials

Title

Description

Actions

Title

DX-CTT-Manuscript-SI

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 - 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 .

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.