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. 2018 Dec 4;10(6):1780-1785.
doi: 10.1039/c8sc04279a. eCollection 2019 Feb 14.

Ni-catalysed reductive arylalkylation of unactivated alkenes

Youxiang Jin  1 , Chuan Wang  1
Affiliations

Ni-catalysed reductive arylalkylation of unactivated alkenes

Youxiang Jin et al. Chem Sci. .

Abstract

In this protocol Ni-catalysed reductive arylalkylation of unactivated alkenes tethered to aryl bromides with primary alkyl bromides has been accomplished, providing a new path to construct diverse benzene-fused carbo- and heterocyclic cores including indanes, tetrahydroisoquinolines, indolines and isochromanes. Notably, this new method circumvents the pregeneration of organometallics and demonstrates high tolerance to a wide range of functional groups. The preliminary mechanistic investigations suggest a reaction pathway with an intermediate reduction.

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Figures

Scheme 1
Scheme 1. Redox-neutral (A) and reductive (B) arylalkylation of tethered alkenes for the synthesis of benzene-fused cyclic compounds.
Scheme 2
Scheme 2. Stoichiometric reactions of bromides 1a and 2a with Zn-powder.
Scheme 3
Scheme 3. Stoichiometric control experiments for the Ni-catalyzed reductive arylalkylation.
Scheme 4
Scheme 4. Radical clock experiment for the Ni-catalyzed reductive arylalkylation.
Scheme 5
Scheme 5. Ni-catalysed arylalkylation employing a chiral oxazoline ligand.
Scheme 6
Scheme 6. Proposed mechanism of the Ni-catalyzed reductive arylalkylation.
See this image and copyright information in PMC

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