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Diarylmethane synthesis through Re_2O_7-catalyzed bimolecular dehydrative Friedel–Crafts reactions

Qin, Qi and Xie, Youwei and Floreancig, Paul E. (2018) Diarylmethane synthesis through Re_2O_7-catalyzed bimolecular dehydrative Friedel–Crafts reactions. Chemical Science, 9 (45). pp. 8528-8534. ISSN 2041-6520. PMCID PMC6251338. https://resolver.caltech.edu/CaltechAUTHORS:20190418-080402772

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Abstract

This manuscript describes the application of Re_2O_7 to the syntheses of diarylmethanes from benzylic alcohols through solvolysis followed by Friedel–Crafts alkylation. The reactions are characterized by broad substrate scope, low catalyst loadings, high chemical yields, and minimal waste generation. The intermediate perrhenate esters are superior leaving groups to chlorides and bromides in these reactions. The polarity and water sequestering capacity of hexafluoroisopropyl alcohol are critical to the success of these processes. Re_2O_7 is a precatalyst for HOReO_3, which serves as a less costly and easily handled promoter for these reactions. Oxorhenium catalysts selectively activate alcohols in the presence of similarly substituted acetates, indicating a unique chemoselectivity and mechanism in comparison to Brønsted acid catalysis.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/c8sc03570aDOIArticle
http://www.rsc.org/suppdata/c8/sc/c8sc03570a/c8sc03570a1.pdfPublisherSupplementary Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6251338PubMed CentralArticle
ORCID:
AuthorORCID
Floreancig, Paul E.0000-0001-9626-3187
Alternate Title:Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions
Additional Information:© 2018 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. The article was received on 11 Aug 2018, accepted on 30 Aug 2018 and first published on 13 Sep 2018. We thank the National Institutes of Health (R01GM103886) for generous funding of this project. The authors declare no competing interests.
Funders:
Funding AgencyGrant Number
NIHR01GM103886
Issue or Number:45
PubMed Central ID:PMC6251338
Record Number:CaltechAUTHORS:20190418-080402772
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20190418-080402772
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:94778
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:18 Apr 2019 20:18
Last Modified:03 Oct 2019 21:07

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