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Stability and Reactivity Trends of Alkylidene Dihydropyridines

Matthew Puzhistky, Andrei Nikolaev, Ekadashi Pradhan, Tao Zeng, Dan Fishlock and Arturo Orellana*

2024, submitted.

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Collaboration with F. Hoffmann - La Roche.

Mild and Catalytic Electrocyclization of Heptatrienyl Anions

Faizan Rasheed, Andrei Nikolaev, Anmol Dhesi, Tao Zeng, You Xuan Guo, Yarkali Krishna, Samira Komijani and

Arturo Orellana*

2024, submitted

The Electrocyclization of Heptatrienyl Anions

Samira Komijani and Arturo Orellana*

Synthesis 2024, 56, 701

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Soft Fluorination of 4-Alkylpyridines

Faizan Rasheed, Jiaqi Shi, Tao Zeng, Yarkali Krishna, Dan Fishlock and Arturo Orellana*

Organic Letters 2023, 25, 8628

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Collaboration with F. Hoffmann - La Roche.

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Mild Installation of Piperidines on 4-Alkylpyridines

Jiaqi Shi, Faizan Rasheed, Dan Fishlock and Arturo Orellana*

Organic Letters 2023, 25, 4852.

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Collaboration with F. Hoffmann - La Roche.

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Highlighted in Organic Process Research and Development 2023, 27, 1535.

The Omega(3) Hydroxy Fatty Acid 7(S)-HDHA is a High-Affinity PPAR-alpha Ligand that Regulates Brain Neuronal Morphology.

Jiabao Liu, Cigdem Sahin, Samar Ahmad, Lilia Magomedova, Minho Zhang, Zhengping Jia, Adam H. Metherel, Arturo Orellana, Gennady Poda, Richard P. Bazinet, Liliana Attisano, Carolyn L. Cummins, Hui Peng and Henry Krause*

Science Signalling 2022,15, 741.

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Collaboration with Henry Krause - Donnelly Center for Cellular and Biomolecular Research, University of Toronto

Alkylidene Dihydropyridines are Surrogates for Pyridylic Anions in the Conjugate Addition to Unsaturated Ketones.

Jiaqi Shi, Ashik A. Sayyad, DanFishlock and Arturo Orellana*

Organic Letters 2022, 24, 48.

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Collaboration with F. Hoffmann - La Roche

Palladium-Catalyzed Mild Dehydrogenation of 4-Alkylpyridines

Nour Wasfy, Faizan Rasheed, Brian Doan, Dan Fishlock and Arturo Orellana*

ACS Catalysis 2021,11, 3251.

We disclose a very mild and general method to prepare 4-alkenylpyridines, which are useful building blocks in drug discovery.

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Collaboration with F. Hoffmann - La Roche

Pyridylic Anions are Soft Nucleophiles in the Palladium-Catalyzed Allylation of Alkylpyridines

Nour Wasfy, Faizan Rasheed, Raphael Robidas, Isabelle Hunter, Jiaqi Shi, Brian Doan, Claude Y. Legault,* Dan Fishlock and Arturo Orellana*

Chemical Science 2021,12, 1503.

We develop an exceptionally mild method for the selective allylation of 4-alkylpyridines.

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Collaboration with F. Hoffmann - La Roche.

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highlighted in SYNFACTS 2021, 17, 293

Enantioselective Synthesis of 7(S)-Hydroxydocosahexaenoic Acid,

a Possible Endogenous Ligand for PPAR-alpha

Minhao Zhang, Ashik A. Sayyad, Anmol Dhesi and Arturo Orellana*

The Journal of Organic Chemistry 2020, 85, 13621.

We report the first total synthesis of this biologically important natural product.

The Acid-Free Cyclopropanol-Minisci Reaction Reveals the Catalytic Activity of Silver-Pyridine Complexes

Andrei Nikolaev, Claude Y. Legault, Minhao Zhang and Arturo Orellana*

Organic Letters 2018, 20, 796-799.

We developed a method for direct alkylation of pyridines and related heterocycles using a well-defined silver catalyst. Along the way we uncovered the catalytic activity of in-situ formed silver-heterocycle complexes.

Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki Coupling and Oxidation

Zi Wang and Arturo Orellana*

Chemistry - A European Journal 201723, 11445

We develop a new method for the synthesis of meta-substituted phenols by merging the Suzuki-Miyaura reaction and the palladium-catalyzed oxidation of cyclohexenones to phenols.

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Chosen as a VIP contribution by the editorial board

Separating the Inflammatory and Diabetogenic Effects of Glucocorticoids Through LXR-beta Antagonism

Rucha Patel, Lilia Magovedova, Ricky Tsai, Stephane Angers, Arturo Orellana and Carolyn Cummins*

Endocrinology 2017, 158, 1034

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Collaboration with Carolyn Cummins - Leslie Dan School of Pharmacy, University of Toronto.

A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of g,d-Unsaturated Ketones

Sadaf Samadi and Arturo Orellana*

ChemCatChem 20168, 2472.

We describe a conceptually new method for the synthesis of substituted phenols that avoids many of the limitiations inherent in other routes.

Synthesis of a,b-Unsaturated Acyl Silanes via Perrhenate-Catalyzed Meyer-Schuster Rearrangement of 1-Silylalkyn-3-ols.

Andrei Nikolaev and Arturo Orellana*

Organic Letters 2015, 17, 5796

We develop a practical route to acyl silanes. The substrates are easily prepared by addition of silylated acetylenes to aldehydes or ketones. A variety of acyl silanes are prepared in good yields.

Transition Metal-Catalyzed C-C and C-X Bond-Forming Reactions Using Cyclopropanols

Andrei Nikolaev and Arturo Orellana*

Synthesis 2016, 48, 1741

A comprehensive review of the literature from 2000 to 2016.

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Invited Review

Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols

David Rosa, Andrei Nikolaev, Nisha Nithiy and Arturo Orellana*

Synlett 2015, 26, 441

A review of the use of cyclopropanols in palladium-catalyzed C-C bond formation.

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Invited Account

Palladium-Catalyzed Cross-Coupling of Benzyl Chlorides with Cyclopropanol-Derived Palladium Homoenolates

Nisha Nithiy and Arturo Orellana*

Organic Letters 2014, 16, 5854

We extend the range of oxidative addition partners that can be used in palladium-catalyzed cross-coupling reactions of cyclopropanols. 

One-Step Synthesis of Quinolines via Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Unprotected ortho-Bromoanilines

Andrei Nikolaev, Nisha Nithiy and Arturo Orellana*

Synlett 2014, 25, 2301

We develop a cascade reaction of cyclopropanols with bromoanilines.

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Invited Contribution

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Featured in the Organic Chemistry Portal

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Highlighted in SYNFACTS

Liver X Receptors Preserve Renal Gromerular Integrity Under Normoglycaemia and in Diabetes in Mice

M. Patel, X. Wang, R. John, L. Magomedova, A. Rasheed, H. Santamaria, W. Wang, R. Tsai, L. Qiu,  A. Orellana, M. Levi, C. Cummins*

Diabetologia, 2014, 57, 435

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Collaboration with Carolyn Cummins - Leslie Dan School of Pharmacy, University of Toronto.

Carbon-Carbon Bond Formation Through Palladium Homoenolates

David Rosa, Nisha Nithiy and Arturo Orellana*

Synthesis, 2013, 45, 3199

We review all the methods known to generate palladium-homoenolates and their use in C-C cross-coupling.

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Invited Review

Potassium Acetate

Arturo Orellana*

Encyclopedia of Reagents for Organic Synthesis 2013

Palladium-Catalyzed Cross-Coupling of Cyclopropanol-Derived Ketone Homoenolates with Aryl Bromides

David Rosa and Arturo Orellana*

Chemical Communications 201349, 5420

We report the cross coupling of palladium homolates with aryl bromides. Judicious choice of ligands on palladium enables the coupling homoenolates with b-hydrides, extending  the range of cyclopropanols that can be used in this reaction.

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Featured in the Organic Chemistry Portal

Measuring Kinetic Isotope Effects in Enzyme Reactions Using Time-Resolved Electrospray Mass Spectrometry

Peter Liuni, Ekaterina Olkhov-Mitsel,  Arturo Orellana and Derek Wilson*

Analytical Chemistry 2013, 85, 3758

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Collaboration with Professor Derek Wilson - Center for Research in Mass Spectrometry

Tandem Decarboxylative Allylation and Fragmentation of Allyl-benzocyclobutenyl Carbonates: Access to ortho-Functionalized Aryls from Aryl Bromides.

David Rosa, Andrei Chtchemelinine and Arturo Orellana*

Synthesis 2012, 44, 1885

We merge the palladium-catalyzed selective cleavage of benzocyclobutenols with decarboxylative allylation chemistry.

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Invited Contribution

Palladium-Catalyzed Synthesis of Acyl Pyrroles from Aryl Iodides

Stephanie Ho, Ganna Bondarenko, David Rosa, Bojan Dragisic and Arturo Orellana*

The Journal of Organic Chemistry 2012, 77, 2008

We develop a new route to acyl pyrroles, which serve as surrogates to Weinreb amides. This work was primarily conducted by undergraduate thesis students.

Synthesis of 1-Indanones via Intramolecular Direct Arylation with Cyclopropanol-Derived Palladium Homoenolates

David Rosa and Arturo Orellana*

Chemical Communications 2012, 48, 1922

This is one of the first reports using alkylpalladium intermediates in direct arylation chemistry.

Palladium-Catalyzed Selective Carboelimination and Cross-Coupling Reactions of Benzocyclobutenols.

Andrei Chtchemelinine, David Rosa and Arturo Orellana*

The Journal of Organic Chemistry 2011, 76, 9157

We report the first controlled cleavage and C-C bond forming reaction of benzocyclobutenols.

Palladium-Catalyzed Oxidative Rearrangement of Diaryl Alkenyl Carbinols to b,b-Diaryl-a,b-Unsaturated Ketones.

David Rosa and Arturo Orellana*

Organic Letters 2011, 13, 3648

We describe a very unusual, palladium-catalyzed rearrangement of tertiaryl allylic alcohols to ketones with rearrangement of the carbon framework.

Synthesis of benzodiquinanes via Tandem Palladium-Catalyzed Semipinacol Rearrangement and Direct Arylation.

Angelika Schweinitz, Andrei Chtchemelinine and Arturo Orellana*

Organic Letters 2011, 13, 232

We merge the palladium-catalyzed semipinacol rearrangement with direct arylation chemistry.

Palladium-Catalyzed Coupling of Cyclopropanols with Aryl Halides Under Mild Conditions.

David Rosa and Arturo Orellana*

Organic Letters 2011, 13, 110

We report the first cross-coupling reaction of cyclopropanols with aryl halides. 

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