Publications 2020-2022

Journal Articles

2022

Exploring Photoredox-Catalyzed (Re)functionalizations with Core-Modified Benziodoxolones
Stephanie G. E. Amos, Franck Le Vaillant and Jerome Waser
Helv. Chim. Acta 2022, e202200161. (10.1002/hlca.202200161) Green Access

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Substrate-controlled C–H or C–C alkynylation of cyclopropanes: generation of aryl radical cations by direct light activation of hypervalent iodine reagents
Tin V. T. Nguyen, Matthew D. Wodrich and Jerome Waser
Chem. Sci. 2022, 13, 12831-12839. (10.1039/D2SC04344K) Open Access! Raw data

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Tyrosine bioconjugation with hypervalent iodine
Nina Declas, John R. J. Maynard, Laure Menin, Natalia Gasilova, Sebastian Götze, Jakob L. Sprague, Pierre Stallforth, Stefan Matile and Jerome Waser
Chem. Sci. 2022, 13, 12808-12817. (10.1039/D2SC04558C) Open Access! Raw data

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Copper-Catalyzed Alkynylation of Hydrazides: An Easy Access to Functionalized Azadipeptides
Eliott Le Du, Julien Borrel, and Jerome Waser
Org. Lett. 2022, 24, 6614–6618. (10.1021/acs.orglett.2c02625) Green Access Raw data

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(4+3) Annulation of Donor-Acceptor Cyclopropanes and Azadienes: Highly Stereoselective Synthesis of Azepanones
Stefano Nicolai* and Jerome Waser*
Angew. Chem., Int. Ed. 2022, 61, e202209006. (10.1002/anie.202209006) Raw data Open Access!

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Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation
Thomas Rossolini, Ashis Das, Stefano Nicolai and Jerome Waser
Org. Lett. 2022, 24, 5068-5072. (10.1021/acs.orglett.2c01838) Raw data Open Access!

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Palladium-Catalyzed trans-Hydroalkoxylation: Counterintuitive Use of an Aryl Iodide Additive to Promote C–H Bond Formation
Ashis Das, Luca Buzzetti, Mikus Puriņš and Jerome Waser
ACS catal. 2022, 12, 7565-7570. (10.1021/acscatal.2c01809) Raw data Open Access!

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Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives
Emma G. L. Robert, Eliott Le Du and Jerome Waser
Chem. Commun. 2022, 58, 3473-3476. (10.1039/D2CC00167E) Raw data Green Access

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N-Terminal Selective C−H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification
Emmanuelle M. D. Allouche, Raphael Simonet-Davin and Jerome Waser
Chem. Eur. J. 2022, 28, e202200368. (10.1002/chem.202200368) Raw data Open Access!

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Asymmetric Cyclopropanation and Epoxidation via a Catalytically Formed Chiral Auxiliary
Mikus Purins and Jerome Waser
Angew. Chem., Int. Ed. 2022, 61, e202113925. (10.1002/anie.202113925) Raw data Open Access!

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2021

Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations
Julien Borrel and Jerome Waser
Org. Lett. 2022, 23, 142-146. (10.1021/acs.orglett.1c03771) Green Access Raw data

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Direct Photoexcitation of EthynylBenziodoXolones: An Alternative to Photocatalysis for Alkynylation Reaction
Stephanie G. E. Amos, Diana Cavalli, Franck Le Vaillant and Jerome Waser
Angew. Chem., Int. Ed. 2021, 60, 23827-23834. (10.1002/anie.202110257) Raw data Open Access!

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Diamine Synthesis via the Nitrogen-Directed Azidation of σ- and π-C-C Bonds
Ming-Ming Wang, Tin V. T. Nguyen and Jerome Waser
J. Am. Chem. Soc. 2021, 143, 11969–11975. (10.1021/jacs.1c06700) Green Access Raw data

Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines
Nieves P. Ramirez, Guillaume Pisella and Jerome Waser
J. Org. Chem. 2021, 86 , 10928–10938. (10.1021/acs.joc.1c01423) Green Access Raw data

Inhibition of Thiol-Mediated Uptake with Irreversible Covalent Inhibitors
Bumhee Lim, Yangyang Cheng, Takehiro Kato, Anh-Tuan Pham, Eliott Le Du, Abhaya Kumar Mishra, Elija Grinhagena, Dimitri Moreau, Naomi Sakai, Jerome Waser and Stefan Matile
Helv. Chim. Acta 2021, 104, e2100085. (10.1002/hlca.202100085) Open Access!

Collaboration: The biological screenings were performed at the Matile group .

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
Vladyslav Smyrnov, Bastian Muriel and Jerome Waser
Org. Lett. 2021, 23, 5435-5439. (10.1021/acs.orglett.1c01775) Green Access Raw data

Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
Abhaya Kumar Mishra, Romain Tessier, Durga Prasad Hari and Jerome Waser
Angew. Chem., Int. Ed. 2021, 60, 17963-17968. (10.1002/anie.202106458) Open Access!

Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents
Eliott Le Du, Thibaut Duhail, Matthew D. Wodrich, Rosario Scopelliti, Farzaneh Fadaei-Tirani, Elsa Anselmi, Emmanuel Magnier and Jerome Waser
Chem. Eur. J. 2021, 27, 10979-10986. (10.1002/chem.202101475) Raw data Open Access!

Collaboration: The preparation of sulfoximine precursors was performed at the Magnier Group at the Institut Lavoisier de Versailles .

Catalytic (3+2) Annulation of Donor-Acceptor Aminocyclopropane Monoesters and Indoles
Vincent Pirenne, Emma G. L. Robert and Jerome Waser
Chem. Sci. 2021, 12, 8706-8712. (10.1039/D1SC01127H) Raw data Open Access!

Cys‐Cys and Cys‐Lys Stapling of Unprotected Peptides Enabled by Hypervalent Iodine Reagents
Javier Ceballos, Elija Grinhagena, Gontran Sangouard, Christian Heinis and Jerome Waser
Angew. Chem., Int. Ed. 2021, 60, 9022-9031. (10.1002/anie.202014511) Open Access!

Collaboration: The binding affinity of the stapled peptides was measured at the Heinis group .

Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification
Eliott Le Du, Marion Garreau and Jerome Waser
Chem. Sci. 2021, 12, 2467-2473. (10.1039/d0sc06180h) Raw data Open Access!

2020

Low‐Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands
Durga Prasad Hari, Guillaume Pisella, Matthew D. Wodrich, Artem V. Tsymbal, Farzaneh Fadaei Tirani, Rosario Scopelliti and Jerome Waser
Angew. Chem., Int. Ed. 2021, 60, 5475-5481. (10.1002/anie.202012299) Green Access

Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds
Bastian Muriel and Jerome Waser
Angew. Chem., Int. Ed. 2021, 60, 4075-4079. (10.1002/anie.202013516) Raw data Green Access

Synthesis of Thiochromans via [3+3] Annulation of Aminocyclopropanes with Thiophenols
Ming-Ming Wang, Seongmin Jeon and Jerome Waser
Org. Lett. 2020, 22, 9123-9127. (10.1021/acs.orglett.0c03528) Raw data Green Access

Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary
Luca Buzzetti, Mikus Purins, Phillip D. G. Greenwood and Jerome Waser
J. Am. Chem. Soc. 2020, 142, 17334-17339. (10.1021/jacs.0c09177 ) Raw data Open Access!

Photocatalytic Umpolung of N- and O- Substituted Alkenes for the Synthesis of 1,2-Amino Alcohols and Diols
Stephanie G. E. Amos, Stefano Nicolai and Jerome Waser
Chem. Sci. 2020, 11, 11274-11279. (10.1039/D0SC03655B ) Raw data Open Access!

Photochemical Functionalization of Heterocycles with EBX Reagents; C‐H Alkynylation versus Deconstructive Ring Cleavage
Errika Voutyritsa, Marion Garreau, Maroula G. Kokotou, Ierasia Triandafillidi, Jérôme Waser and Christoforos G. Kokotos
Chem. Eur. J. 2020, 26, 14453-14460. (10.1002/chem.202002868 ) Green Access

Collaboration: The photoredox chemistry was developed at the Kokotos group .

Oxidative Fluorination of Cyclopropylamides via Organic Photoredox Catalysis
Ming-Ming Wang and Jerome Waser
Angew. Chem., Int. Ed. 2020, 59, 16420-16424. (10.1002/anie.202007864 ) Raw data Green Access

Access to Vinyl Ethers and Ketones with Hypervalent Iodine Reagents as Oxy‐Allyl Cation Synthetic Equivalents
Nina Declas and Jerome Waser
Angew. Chem., Int. Ed. 2020, 59, 18256-18260. (10.1002/anie.202006707 ) Raw data Green Access

Triazene-Activated Donor–Acceptor Cyclopropanes: Ring-Opening and (3 + 2) Annulation Reactions
Abdusalom A. Suleymanov, Eliott Le Du, Zhaowen Dong, Bastian Muriel, Rosario Scopelliti, Farzaneh Fadaei-Tirani, Jérôme Waser and Kay Severin
Org. Lett. 2020, 22, 10, 4517-4522. (10.1021/acs.orglett.0c01527 ) Raw data Green Access

Collaboration: The triazene chemistry was developed at the Severin group .

Copper-Catalyzed Oxyvinylation of Diazo Compounds
Guillaume Pisella, Alec Gagnebin and Jerome Waser
Org. Lett. 2020, 22, 10, 3884–3889. (10.1021/acs.orglett.0c01150 ) Raw data Green Access

Ethynylation of Cysteines from Peptides to Proteins in Living Cells
Romain Tessier, Raj Kumar Nandi, Brendan G. Dwyer, Daniel Abegg, Charlotte Sornay, Javier Ceballos, Stephane Erb, Sarah Cianferani, Alain Wagner, Guilhem Chaubet and Jerome Waser
Angew. Chem., Int. Ed. 2020, 59, 10961-10970. (10.1002/anie.202002626 ) Green Access

Collaboration: Antibody modification studies were done in the Wagner/Chaubet group and proteomic studies were done in the Adibekian group .

Three‐Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers
Guillaume Pisella, Alec Gagnebin and Jerome Waser
Chem. Eur. J. 2020, 26, 10199-10204. (DOI:10.1002/chem.202001317 ) Green Access

Copper-Catalyzed Oxyalkynylation of C–S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents
Julien Borrel, Guillaume Pisella and Jerome Waser
Org. Lett. 2020, 22, 422-427. (DOI:10.1021/acs.orglett.9b04157 ) Raw data Green Access

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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
Durga Prasad Hari, Paola Caramenti, Lionel Schouwey, Miyeon Chang, Stefano Nicolai, Donald Bachert, Timothy Wright, Chuck Orella and Jerome Waser
Org. Process Res. Dev. 2020, 24, 106-110. (DOI:10.1021/acs.oprd.9b00498) Green Access

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Review Articles

2022

Pd-catalyzed functionalization of alkenes and alkynes using removable tethers
Ashis Das and Jerome Waser
Tetrahedron 2022, 128, 133135. (DOI:10.1016/j.tet.2022.133135) Open Access!

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Azidation with Hypervalent Iodine Reagents
Raphael Simonet-Davin and Jerome Waser
Synthesis 2022, in press. (DOI:10.1055/a-1966-4974) Green Access!

Activation of Aminocyclopropanes via Radical Intermediates
Ming-Ming Wang, Tin V. T. Nguyen and Jerome Waser
Chem. Soc. Rev.  2022, 51, 7344-7357. (DOI:10.1039/D2CS00090C) Green Access!

Radical Alkynylations with EthynylBenziodoXolones: from Photocatalysis to Direct Excitation
Stephanie G. E. Amos and Jerome Waser
Chimia 2022, 76, 312. (DOI:10.2533/chimia.2022.312) Open Access!

2021

Hypervalent Iodine-Mediated Late-Stage Peptide and Protein Functionalization
Emmanuelle M. D. Allouche, Elija Grinhagena and Jerome Waser
Angew. Chem. Int. Ed. 2022, 61, e202112287. (DOI:10.1002/anie.202112287) Open Access!

Umpolung of Electron-Rich Heteroarenes with Hypervalent Iodine Reagents
Pamela Pal, Jerome Waser, and Raj Kumar Nandi
Heterocycles 2021, 103, 555-591. (DOI:10.3987/COM-20-S(K)33) Special Issue in honor of Yasuyuki Kita.

2020

Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)
Stefano Nicolai, Ugo Orcel, Bastian Muriel, Phillip D. G. Greenwood, Luca Buzzetti, Mikus Purins and Jerome Waser
Synlett 2021, 32, 472-487. (DOI: 10.1055/a-1308-0021 ) Green Access

Vinylbenziodoxol(on)es: Synthetic Methods and Applications
Nina Declas, Guillaume Pisella and Jerome Waser
Helv. Chim. Acta 2020, 103, e2000191. (DOI: 10.1002/hlca.202000191 ) Green Access

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes
Vincent Pirenne, Bastian Muriel, and Jerome Waser
Chem. Rev. 2021, 121, 227-263. (DOI: 10.1021/acs.chemrev.0c00109 ) Green Access

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis
Stephanie G. E. Amos, Marion Garreau, Luca Buzzetti and Jerome Waser
Beilstein J. Org. Chem. 2020, 16, 1163-1187. (DOI: 10.3762/bjoc.16.103 ) Open Access!

1‐Azido‐3,3‐dimethyl‐3‐(1H )‐1,2‐benziodoxole
Raphael Simonet-Davin and Jerome Waser
Electronic Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2020. (DOI: 10.1002/047084289X.rn02312 )