The -butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to as well as and isomeric series.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9007461 | PMC |
| http://dx.doi.org/10.1021/acs.joc.1c03160 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Access to Diarylmethanols by Wittig Rearrangement of , , and Benzyloxy--Butylbenzamides.
J Org Chem
April 2022
EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, U.K.
The -butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to as well as and isomeric series.
View Article and Find Full Text PDFAccess to Diarylmethanol Skeletons via a Samarium/Copper-Mediated Sequential Three-Component C-H Functionalization Reaction.
J Org Chem
July 2021
Key Laboratory of Optic-Electric Sensing and Analytical Chemistry for Life Science, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
A novel three-component reaction was developed via a one-pot strategy for the construction of diarylmethanol esters by using a halobenzene and an ester in ,-dimethylformamide (DMF) under mild conditions. The reaction involves the direct functionalization of halobenzene under the Sm-CuI catalyst system. It was proved that 10% (mol) of CuI is sufficient to realize the reductive coupling reaction.
View Article and Find Full Text PDFA selective removal of the secondary hydroxy group from -dithioacetal-substituted diarylmethanols.
Beilstein J Org Chem
May 2018
Group of Synthesis of Functional Materials, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.
We present a successful deoxygenation reaction of -1,3-dithianylaryl(aryl)methanols which enables a selective removal of the secondary hydroxy group in presence of the 1,3-dithianyl moiety under reductive conditions. This reaction proceeds well with ZnI/Na(CN)BH in dichloroethane or benzene for both unsubstituted and substituted aryls (by electron-rich groups). This is leading to formyl-protected diarylmethanes with potential application in the synthesis of new pharmaceuticals and optoelectronic materials.
View Article and Find Full Text PDFEfficient Access to Chiral Benzhydrols via Asymmetric Transfer Hydrogenation of Unsymmetrical Benzophenones with Bifunctional Oxo-Tethered Ruthenium Catalysts.
J Am Chem Soc
August 2016
Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
A concise asymmetric transfer hydrogenation of diaryl ketones, promoted by bifunctional Ru complexes with an etherial linkage between 1,2-diphenylethylenediamine (DPEN) and η(6)-arene ligands, was successfully developed. Because of the effective discrimination of substituents at the ortho position on the aryl group, unsymmetrical benzophenones were smoothly reduced in a 5:2 mixture of formic acid and triethylamine with an unprecedented level of excellent enantioselectivity. For the non-ortho-substituted benzophenones, the oxo-tethered catalyst electronically discerned biased substrates, resulting in attractive performance yielding chiral diarylmethanols with >99% ee.
View Article and Find Full Text PDFThe Barbier-Grignard-type arylation of aldehydes using unactivated aryl iodides in water.
Nat Commun
June 2014
Department of Chemistry and FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 0B8.
Carbon-carbon bond formation is the essence of organic synthesis. One of the most important methods for forming carbon-carbon bonds is the Barbier-Grignard-type reaction, which was discovered over a century ago. However, it is still highly desirable to further improve this process.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!