Publications by Durga Prasada Rao Hari

X-Ray and NMR Structural Data of Ethynylbenziodoxolones (EBXs) Reagents and Their Analogues

Rosario Scopelliti, Matthew Wodrich, Jérôme Waser, Stefano Nicolai, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Eliott Hugo Joran Le Du, Nieves Pilar Ramirez Hernandez

First synthesized in 1991, EthynylBenziodoXolones (EBXs) - cyclic hypervalent iodine reagents derived from 2-iodobenzoic acid - are now among the most versatile electrophilic alkynylation reagents. Due to their cyclic structure, these reagents exhibit enha ...

WILEY-V C H VERLAG GMBH2023

Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water

Jérôme Waser, Durga Prasada Rao Hari, Romain Gaëtan Tessier, Abhaya Kumar Mishra

We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent o ...

Wiley-VCH Verlag GmbH2021

Low‐Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands

Rosario Scopelliti, Matthew Wodrich, Jérôme Waser, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Guillaume Dominique Pisella, Artem Tsymbal

The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one‐pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) and ...

Wiley-VCH Verlag GmbH2020

One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability

Jérôme Waser, Stefano Nicolai, Lionel Schouwey, Durga Prasada Rao Hari, Paola Caramenti, Miyeon Chang

The hypervalent iodine reagent 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step fr ...

2019

Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds

Rosario Scopelliti, Jérôme Waser, Lionel Schouwey, Farzaneh Fadaei Tirani, Durga Prasada Rao Hari, Verity Barber

Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, the first syn ...

2019

Cyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung

Jérôme Waser, Durga Prasada Rao Hari, Paola Caramenti

2018

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Jérôme Waser, Durga Prasada Rao Hari

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usin ...

2017

Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation

Jérôme Waser, Maria Victoria Vita, Yifan Li, Durga Prasada Rao Hari

Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their ...

Wiley-Blackwell2016

Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents

Jérôme Waser, Durga Prasada Rao Hari

Alkynes have found widespread applications in synthetic chemistry, biology, and materials sciences. In recent years, methods based on electrophilic alkynylation with hypervalent iodine reagents have made acetylene synthesis more flexible and efficient, but ...

American Chemical Society2016

Proteome-Wide Profiling of Targets of Cysteine reactive Small Molecules by Using Ethynyl Benziodoxolone Reagents

Jérôme Waser, Chao Wang, Reto Frei, Durga Prasada Rao Hari

In this study, we present a highly efficient method for proteomic profiling of cysteine residues in complex proteomes and in living cells. Our method is based on alkynylation of cysteines in complex proteomes using a clickable alkynyl benziodoxolone bearin ...

Wiley-Blackwell2015

Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism

Matthew Wodrich, Jérôme Waser, Reto Frei, Durga Prasada Rao Hari

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with ...

2014