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Synthesis 2017; 49(04): 910-916
DOI: 10.1055/s-0035-1561439
DOI: 10.1055/s-0035-1561439
paper
Iridium-Catalyzed C4-Alkylation of 2,6-Di-tert-butylphenol by Using Hydrogen-Borrowing Catalysis
Further Information
Publication History
Received: 24 March 2016
Accepted: 02 April 2016
Publication Date:
12 May 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201704/lookinside/thumbnails/ss-2016-z0210-op_10-1055_s-0035-1561439-1.jpg)
Abstract
An iridium-catalyzed hydrogen-borrowing process has been developed whereby 2,6-di-tert-butylphenol can be alkylated at the C4-position by using a range of primary alcohols (11 examples, 40–93% yield). Following this, a selection of the products obtained underwent retro-Friedel–Crafts reactions to provide para-substituted phenols, which could potentially undergo further synthetic manipulations.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561439.
- Supporting Information
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For recent reviews, see:
Bi(cyclohexadienylidene)dione 4 is not isolable, but has been previously characterized in solution by 1H NMR spectroscopy; see: