Search Results - "Stuart, David R"

Aryl Transfer Selectivity in Metal‐Free Reactions of Unsymmetrical Diaryliodonium Salts by Stuart, David R.

“…Aromatic rings are found in a wide variety of products, including pharmaceuticals, agrochemicals, and functional materials. Diaryliodonium salts are new…”
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Catalytic Cross-Coupling of Unactivated Arenes by Stuart, David R, Fagnou, Keith

“…The industrially important coupling of aromatic compounds has generally required differential prefunctionalization of the arene coupling partners with a halide…”
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Metal-free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution by Sandtorv, Alexander H., Stuart, David R.

“…A mild and metal‐free approach to C−N coupling is described that employs diaryliodonium salt electrophiles and secondary aliphatic amine nucleophiles. This…”
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Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles by Huestis, Malcolm P, Chan, Lina, Stuart, David R, Fagnou, Keith

“…Rho‐Rho‐Rho your boat: A rhodium catalyst effects the regioselective oxidative coupling of enynes with N‐aryl ureas (X=NR2) and N‐vinylacetamides (X=C(O)Me),…”
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Analysis of Benzenoid Substitution Patterns in Small Molecule Active Pharmaceutical Ingredients by Nilova, Aleksandra, Campeau, Louis-Charles, Sherer, Edward C, Stuart, David R

“…Previous analyses have revealed that benzenoid rings are prevalent scaffolds in active pharmaceutical ingredients (APIs). Here, we analyze the substitution…”
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Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers by Gallagher, Rory T., Basu, Souradeep, Stuart, David R.

“…Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way,…”
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A Selective C−H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine by Sundalam, Sunil K., Nilova, Aleksandra, Seidl, Thomas L., Stuart, David R.

“…Described here is an efficient method to access highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts. The iodonium salts are…”
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Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts by Sundalam, Sunil K, Stuart, David R

“…The base mediated coupling of aliphatic alcohol pronucleophiles with unsymmetric diaryliodonium salt electrophiles is described. This metal-free reaction is…”
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Unsymmetrical Aryl(2,4,6-trimethoxy­phenyl)­iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies by Seidl, Thomas L, Sundalam, Sunil K, McCullough, Brennen, Stuart, David R

“…Diaryliodonium salts have recently attracted significant attention as metal-free-arylation reagents in organic synthesis, and efficient access to these salts…”
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Indole Synthesis via Rhodium Catalyzed Oxidative Coupling of Acetanilides and Internal Alkynes by Stuart, David R, Bertrand-Laperle, Mégan, Burgess, Kevin M. N, Fagnou, Keith

“…The oxidative synthesis of highly functionalized indoles from simple anilines and internal alkynes mediated by a rhodium(III) catalyst is described. Good…”
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Intramolecular Pd(II)-Catalyzed Oxidative Biaryl Synthesis Under Air: Reaction Development and Scope by Liégault, Benoît, Lee, Doris, Huestis, Malcolm P, Stuart, David R, Fagnou, Keith

“…New reaction conditions for intramolecular palladium(II)-catalyzed oxidative carbon−carbon bond formation under air are described. The use of pivalic acid as…”
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Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts by Carreras, Virginie, Sandtorv, Alexander H, Stuart, David R

“…The direct synthesis of aryl­(2,4,6-trimethoxy­phenyl)­iodonium trifluoro­acetate salts from aryl iodides is described. Stoichiometric quantities of…”
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Mechanistic Analysis of Azine N-Oxide Direct Arylation: Evidence for a Critical Role of Acetate in the Pd(OAc)2 Precatalyst by Sun, Ho-Yan, Gorelsky, Serge I, Stuart, David R, Campeau, Louis-Charles, Fagnou, Keith

“…Detailed mechanistic studies on the palladium-catalyzed direct arylation of pyridine N-oxides are presented. The order of each reaction component is determined…”
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Orbital analysis of bonding in diarylhalonium salts and relevance to periodic trends in structure and reactivity by Karandikar, Shubhendu S, Bhattacharjee, Avik, Metze, Bryan E, Javaly, Nicole, Valente, Edward J, McCormick, Theresa M, Stuart, David R

“…Diarylhalonium compounds provide new opportunities as reagents and catalysts in the field of organic synthesis. The three center, four electron (3c-4e) bond is…”
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Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis by Campeau, Louis-Charles, Stuart, David R., Leclerc, Jean-Philippe, Bertrand-Laperle, Mégan, Villemure, Elisia, Sun, Ho-Yan, Lasserre, Sandrine, Guimond, Nicolas, Lecavallier, Melanie, Fagnou, Keith

“…Palladium-catalyzed direct arylation reactions are described with a broad range of azine and azole N-oxides. In addition to aspects of functional group…”
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A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors by Javaly, Nicole, McCormick, Theresa M, Stuart, David R

“…Halogen bonding permeates many areas of chemistry. A wide range of halogen-bond donors including neutral, cationic, monovalent, and hypervalent have been…”
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Regioselective Synthesis of 1,2,3,4‐Tetrasubstituted Arenes by Vicinal Functionalization of Arynes Derived from Aryl(Mes)iodonium Salts by Nilova, Aleksandra, Sibbald, Paul A., Valente, Edward J., González‐Montiel, Gisela A., Richardson, H. Camille, Brown, Kevin S., Cheong, Paul Ha‐Yeon, Stuart, David R.

“…Herein, the synthesis of 1,2,3,4‐tetrasubstituted benzenoid rings, motifs found in pharmaceutical, agrochemical, and natural products, is described.[1] In the…”
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Imide arylation with aryl(TMP)iodonium tosylates by Basu, Souradeep, Sandtorv, Alexander H, Stuart, David R

“…Herein, we describe the synthesis of -aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts…”
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Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling by Stuart, David R, Villemure, Elisia, Fagnou, Keith

“…By changing the stoichiometric oxidant and modifying the indole N-substituent in palladium-catalyzed oxidative arene cross-coupling reactions, both C2 and C3…”
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Synthesis of Arynes via Formal Dehydrogenation of Arenes by Roberts, Riley A., Metze, Bryan E., Nilova, Aleksandra, Stuart, David R.

“…Arynes offer immense potential for diversification of benzenoid rings, which occur in pharmaceuticals, agrochemicals, and liquid crystals. However, accessing…”
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