Center for Selective C–H Functionalization
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2 News 130 Publications 78 Members

Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.

Malik, Hasnain A Taylor, Buck L H Kerrigan, John R Grob, Jonathan E Houk, K N Du Bois, J Hamann, Lawrence G Patterson, Andrew W

Published in Chemical science

We outline a strategy to enable non-directed Pd(II)-catalyzed C-H functionalization in the presence of Lewis basic heterocycles. In a high-throughput screen of two Pd-catalyzed C-H acetoxylation reactions, addition of a variety of N-containing heterocycles is found to cause low product conversion. A pyridine-containing test substrate is selected as...

Analyzing Site Selectivity in Rh2(esp)2-Catalyzed Intermolecular C–H Amination Reactions PDF available through Get Fulltext Research

Bess, Elizabeth N. Deluca, Ryan J. Tindall, Daniel J. Oderinde, Martins S. Roizen, Jennifer L. Justin Du Bois Matthew Sigman

Published in Journal of the American Chemical Society

Predicting site selectivity in C-H bond oxidation reactions involving heteroatom transfer is challenged by the small energetic differences between disparate bond types and the subtle interplay of steric and electronic effects that influence reactivity. Herein, the factors governing selective Rh2(esp)2-catalyzed C-H amination of isoamylbenzene deriv...

An Enantiospecific Synthesis of Jiadifenolide

Siler, David A. Jeff Mighion Erik Sorensen

Published in Angewandte Chemie International Edition in English

A Robinson annulation, van Leusen homologation, and a desymmetrizing C-H oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone-derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of ...

Organocatalytic C–H hydroxylation with Oxone® enabled by an aqueous fluoroalcohol solvent system PDF available through Get Fulltext Research

Ashley Adams Justin Du Bois

Published in Advances in Chemical Engineering and Science

Selective hydroxylation of 3° and benzylic C–H bonds is made possible using a non-metal-based catalyst system, Oxone as the terminal oxidant, and an aqueous fluoroalcohol solvent mixture. The choice of solvent is uniquely effective for this process, but seemingly at odds with our finding that H2O promotes reduction of the oxaziridine intermediate. ...

C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines PDF available through Get Fulltext Research

Loach, Richard P. Fenton, Owen S. Amaike, Kazuma Siegel, Dustin S. Ozkal, Erhan Mo Movassaghi

Published in The Journal of Organic Chemistry

A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation–C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-bo...

Speciation and decomposition pathways of ruthenium catalysts used for selective C–H hydroxylation PDF available through Get Fulltext Research

Flender, Cornelia Ashley Adams Roizen, Jennifer L. Mcneill, Eric Justin Du Bois Richard Zare

Published in Advances in Chemical Engineering and Science

Mechanistic insight into a C–H hydroxylation reaction catalysed by [(Me3tacn)RuCl3] has been obtained using desorption electrospray ionization mass spectrometry (DESI-MS) to identify reactive intermediates and to determine the fate of the starting metal complex. Our studies provide direct evidence for the formation of a high-valent dioxo-Ru(VI) spe...

A General Method for Artificial Metalloenzyme Formation through Strain-Promoted Azide–Alkyne Cycloaddition

Hao Yang Srivastava, Poonam Zhang, Chen Jared Lewis

Published in Chem-Bio Informatics Journal

As good as the real thing: Strain‐promoted azide–alkyne cycloaddition can be used to generate artificial metalloenzymes (ArMs) from scaffold proteins containing a p‐azido‐L‐phenylalanine (Az) residue and catalytically active bicyclononyne‐linked cofactors. This method showed broad scope with respect to both the scaffold and cofactor components, and...

Recyclable Silica-Supported Iridium Bipyridine Catalyst for Aromatic C–H Borylation

Fengshou Wu Yan Feng Christopher Jones

Published in ACS Catalysis

Role of N-Acyl Amino Acid Ligands in Pd(II)-Catalyzed Remote C–H Activation of Tethered Arenes

Gui-Juan Cheng Yun-Fang Yang Peng Liu Ping Chen Tian-Yu Sun Gang Li Xinhao Zhang Ken Houk Jin-Quan Yu Yun-Dong Wu ...

Published in Journal of the American Chemical Society

Palladium-Catalyzed Meta-Selective C–H Bond Activation with a Nitrile-Containing Template: Computational Study on Mechan...

Yun-Fang Yang Gui-Juan Cheng Peng Liu Dasheng Leow Tian-Yu Sun Ping Chen Xinhao Zhang Jin-Quan Yu Yun-Dong Wu Ken Houk ...

Published in Journal of the American Chemical Society

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