Marc Adler

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Organization: Northern Illinois University
Department: Department of Chemistry & Biochemistry
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Co-reporter:Vladislav Skrypai;Joseph J. M. Hurley ;Marc J. Adler
European Journal of Organic Chemistry 2016 Volume 2016( Issue 12) pp:2207-2211
Publication Date(Web):
DOI:10.1002/ejoc.201501599

Abstract

Hydrosilanes are cheap, readily available substrates, yet they do not see as extensive use for simple carbonyl reductions as borohydrides. Hydrosilane reducing agents broadly fall into one of two general categories: either a) they are easy to handle and require expensive and/or hazardous additives, or b) they are difficult and/or dangerous to handle. This work details the discovery of mild and functional group compatible conditions utilizing hydrosilatrane for the selective reduction of aryl aldehydes to benzylic alcohols without unwanted formation of ethers or deoxygenated products. This method offers significant advances in silane reductions as silatrane is an air- and moisture-stable yet relatively reactive reducing agent that can be used in benchtop open air reactions.

Co-reporter:Brian M. Muller, Theodore J. Litberg, Reid A. Yocum, Chanté A. Pniewski, and Marc J. Adler
The Journal of Organic Chemistry 2016 Volume 81(Issue 13) pp:5775-5781
Publication Date(Web):June 7, 2016
DOI:10.1021/acs.joc.6b00986
Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch’s scope, scaffolds able to have multiple switching events were also investigated.
Co-reporter:Sami E. Varjosaari, Jeremy P. Hess, Paolo Suating, John M. Price, Thomas M. Gilbert, Marc J. Adler
Tetrahedron Letters 2015 Volume 56(Issue 4) pp:642-645
Publication Date(Web):21 January 2015
DOI:10.1016/j.tetlet.2014.12.013
Synthetic organic chemists generally think of silyl ethers as easier-to-cleave alkyl ethers, frequently neglecting to consider both the unique facets of elemental silicon and the size of commonly used trialkylsilyl protecting groups. In this study, several ortho- and para-silyloxybenzoic acids were investigated spectroscopically and as catalysts for a Friedel–Crafts reaction, with results highlighting some of the underestimated aspects of trialkylsilyloxyl substituents.
Co-reporter:Brian M. Muller, Jesse Mai, Reid A. Yocum and Marc J. Adler  
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 28) pp:5108-5114
Publication Date(Web):06 May 2014
DOI:10.1039/C4OB00398E
The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.
Co-reporter:Jesse Mai, Ermal Hoxha, Caitlin E. Morton, Brian M. Muller and Marc J. Adler  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 21) pp:3421-3423
Publication Date(Web):18 Mar 2013
DOI:10.1039/C3OB40467F
Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch. In this study, a single methoxy substituent is shown to have a significant impact on the equilibrium dynamics of this reaction; this impact is dependent on the site of substitution.
Co-reporter:Brian M. Muller, Jesse Mai, Reid A. Yocum and Marc J. Adler
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 28) pp:NaN5114-5114
Publication Date(Web):2014/05/06
DOI:10.1039/C4OB00398E
The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.
Co-reporter:Jesse Mai, Ermal Hoxha, Caitlin E. Morton, Brian M. Muller and Marc J. Adler
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 21) pp:NaN3423-3423
Publication Date(Web):2013/03/18
DOI:10.1039/C3OB40467F
Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch. In this study, a single methoxy substituent is shown to have a significant impact on the equilibrium dynamics of this reaction; this impact is dependent on the site of substitution.
2-Propen-1-one, 1-(5-fluoro-2-hydroxyphenyl)-3-phenyl-, (2E)-
2-PROPEN-1-ONE, 1-(2-HYDROXYPHENYL)-3-(3-THIENYL)-, (2E)-
2-Propen-1-one, 1-(2-hydroxy-1-naphthalenyl)-3-phenyl-, (2E)-
BENZOIC ACID, 4-[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]-
4H-1-Benzopyran-4-one, 2,3-dihydro-7-methoxy-2-(2-thienyl)-
2-Propen-1-one, 1-(5-fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)-, (2E)-
Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
Benzonitrile, 4-[[tris(1-methylethyl)silyl]oxy]-
2-Propen-1-one, 3-(4-fluorophenyl)-1-(2-hydroxyphenyl)-, (2E)-
2-Propen-1-one, 1-(2-hydroxyphenyl)-3-(1-naphthalenyl)-, (E)-