Publications

journal-articles

2018

Fine-Tuned Organic Photoredox Catalysts for Fragmentation-Alkynylation Cascades of Cyclic Oxime Ethers
Franck Le Vaillant, Marion Garreau, Stefano Nicolai, Ganna Gryn’ova, Clemence Corminboeuf and Jerome Waser
Chem. Sci. 2018, 9, 5883-5889. (DOI:10.1039/C8SC01818A )

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents
Erwann Grenet, Ashis Das, Paola Caramenti and Jerome Waser
Beilstein J. Org. Chem. 2018, 14, 1208-1214. (DOI:10.3762/bjoc.14.102 )

Metal‐Free Oxidative Cross Coupling of Indoles with Electron‐Rich (Hetero)arenes
Paola Caramenti, Raj Kumar Nandi and Jerome Waser
Chem. Eur. J. 2018, in press. (DOI:10.1002/chem.201802142)

Iridium- and Rhodium-Catalyzed Directed C–H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents
Erwann Grenet and Jerome Waser
Org. Lett. 2018, 20, 1473-1476. (DOI:10.1021/acs.orglett.8b00337)

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor Meso-Diaminocyclopropanes
Daniele Perrotta, Ming-Ming Wang and Jerome Waser
Angew. Chem., Int. Ed. 2018, 57, 5120-5123. (DOI:10.1002/anie.201800494)

2017

Bench-Stable Electrophilic Indole and Pyrrole Reagents: Serendipitous Discovery and Use in C–H Functionalization
Paola Caramenti and Jerome Waser
Helv. Chim. Acta 2017, e1700221. (DOI: 10.1002/hlca.201700221 )

Gold-catalyzed domino cyclization–alkynylation reactions with EBX reagents: new insights into the reaction mechanism
Hossein Ghari, Yifan Li, Roohollah Roohzadeh, Paola Caramenti, Jerome Waser and Alireza Ariafard
Dalton Trans. 2017, 46, 12257-12262. (DOI: 10.1039/C7DT03154H)

Collaboration: Computational results obtained in the Ariafard group .

Dearomatization of Electron Poor Six-Membered N-Heterocycles through [3+2] Annulation with Aminocyclopropanes
Johannes Preindl, Shyamal Chakrabarty and Jerome Waser
Chem. Sci. 2017, 8, 7112-7118. (DOI:10.1039/C7SC03197A )

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung
Paola Caramenti, Stefano Nicolai and Jerome Waser
Chem. Eur. J. 2017, 23, 14702-14706. (DOI: 10.1002/chem.201703723 )

Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds
Durga Prasad Hari and Jerome Waser
J. Am. Chem. Soc. 2017, 139, 8420-8423. (DOI: 10.1021/jacs.7b04756)

Palladium-Catalyzed Carboamination of Allylic Alcohols Using a Trifluoroacetaldehyde-Derived Tether
Bastian Muriel, Ugo Orcel and Jerome Waser
Org. Lett. 2017, 19, 3548–3551. (DOI: 10.1021/acs.orglett.7b01524 )

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents
Sebastien Alazet, Franck Le Vaillant, Stefano Nicolai, Thibaut Courant and Jerome Waser
Chem. Eur. J. 2017, 23, 9501-9504. (DOI: 10.1002/chem.201702599 )

Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole Transport Properties
Yifan Li, Ganna Gryn’ova, Felipe Saenz, Xavier Jeanbourquin, Kevin Sivula, Clemence Corminboeuf and Jerome Waser
Chem. Eur. J. 2017, 23, 8058-8065. (DOI: 10.1002/chem.201701139 )

Collaboration: Computational results obtained in the Corminboeuf group and materials measurements done in the Sivula group .

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation
Franck Le Vaillant, Matthew D. Wodrich and Jerome Waser
Chem. Sci. 2017, 8, 1790-1800. (DOI: 10.1039/C6SC04907A )

2016

One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination
Ugo Orcel and Jerome Waser
Angew. Chem., Int. Ed. 2016, 55, 12881-12885. (DOI: 10.1002/anie.201607318)

Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
Sophie Racine, Bence Hegedus, Rosario Scopelliti and Jerome Waser
Chem. Eur. J. 2016, 22, 11997-12001. (DOI: 10.1002/chem.201602755Green Access

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX
Gergely L. Tolnai, Jonathan P. Brand and Jerome Waser
Beilstein J. Org. Chem. 2016, 12, 745-749. (DOI: 110.3762/bjoc.12.74) Open Access!

Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds with Hypervalent Iodine Reagents
Durga Prasad Hari and Jerome Waser
J. Am. Chem. Soc. 2016, 138, 2190-2193. (DOI: 10.1021/jacs.6b00278Green Access

Nucleoside Analogues: Synthesis from Strained Rings
Sophie Racine, Jeremy Vuilleumier and Jerome Waser
Isr. J. Chem. 2016, 56, 566-577. (DOI: 10.1002/ijch.201500090Green Access

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: alpha- or beta- pi-Addition?
Matthew D. Wodrich, Paola Caramenti and Jerome Waser
Org. Lett. 2016, 18, 60-63. (DOI: 10.1021/acs.orglett.5b03241) Open Access!

2015

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation
Maria Victoria Vita, Paola Caramenti and Jerome Waser
Org. Lett. 2015, 17, 5832-5835. (DOI: 10.1021/acs.orglett.5b03002Green Access

Room-Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents
Franck Le Vaillant, Thibaut Courant and Jerome Waser
Angew. Chem., Int. Ed. 2015, 54, 11200–11204. (DOI: 10.1002/anie.201505111Green Access

Proteome-Wide Profiling of Targets of Cysteine-reactive Small Molecules by using Ethynyl Benziodoxolone Reagents
Daniel Abegg, Reto Frei, Luca Cerato, Durga Prasad Hari, Chao Wang, Jerome Waser and Alexander Adibekian
Angew. Chem., Int. Ed. 2015, 54, 10852–10857. (DOI: 10.1002/anie.201505641)

Collaboration: Biological results obtained in the Adibekian group at the University of Geneva.

Intramolecular Palladium-Catalyzed Alkene Carboalkynylation
Stefano Nicolai, Peter Swallow and Jerome Waser
Tetrahedron 2015, 71, 5959–5964. (DOI: 10.1016/j.tet.2015.06.030Green Access

Platinum-Catalyzed Domino Reaction with Benziodoxole Reagents for Accessing Benzene-Alkynylated Indoles
Yifan Li and Jerome Waser
Angew. Chem., Int. Ed. 2015, 54, 5438-5442. (DOI: 10.1002/anie.201412321Green Access

Palladium-Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by in Situ Tether Formation and Carboetherification
Ugo Orcel and Jerome Waser
Angew. Chem., Int. Ed. 2015, 54, 5250-5254. (DOI: 10.1002/anie.201500636Green Access

[4+2]-Annulations of Aminocyclobutanes
Daniele Perrotta, Sophie Racine, Jeremy Vuilleumier, Florian de Nanteuil and Jerome Waser
Org. Lett. 2015, 17, 1030-1033. (DOI: 10.1021/acs.orglett.5b00149Green Access

One-Pot, Three-Component Arylalkynyl Sulfone Synthesis
C. Chun Chen and Jerome Waser
Org. Lett. 2015, 17, 736-739. (DOI: 10.1021/acs.orglett.5b00015) Open Access!

General and Practical Formation of Thiocyanates from Thiols
Reto Frei, Thibaut Courant, Matthew D. Wodrich and Jerome Waser
Chem. Eur. J. 2015, 21, 2662-2668. (DOI: 10.1002/chem.201406171Green Access

2014

Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism
Reto Frei, Matthew D. Wodrich, Durga Prasad Hari, Pierre-Antoine Borin, Clement Chauvier and Jerome Waser
J. Am. Chem. Soc. 2014, 136, 16563-16573. (DOI: 10.1021/ja5083014) Open Access!

Enantioselective Synthesis of Polycyclic Carbocycles via an Alkynylation–Allylation–Cyclization Strategy
Maria Victoria Vita, Pacal Mieville and Jerome Waser
Org. Lett. 2014, 16, 5768-5771. (DOI: 10.1021/ol5028333Green Access

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents
C. Chun Chen and Jerome Waser
Chem. Commun. 2014, 50, 12923-12926. (DOI: 10.1039/C4CC06851C Green Access

Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions
Eloisa Serrano, Florian de Nanteuil and Jerome Waser
Synlett 2014, 25, 2285-2288. (DOI: 10.1055/s-0034-1378512Green Access

Synthesis of (Carbo)nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes
Sophie Racine, Florian de Nanteuil, Eloisa Serrano and Jerome Waser
Angew. Chem., Int. Ed. 2014, 53, 8484-8487. (DOI: 10.1002/anie.201404832Green Access

Dynamic Kinetic Asymmetric [3 + 2] Annulation Reactions of Aminocyclopropanes
Florian de Nanteuil, Eloisa Serrano, Daniele Perrotta and Jerome Waser
J. Am. Chem. Soc. 2014, 136, 6239-6242. (DOI: 10.1021/ja5024578Green Access

2013

Total Synthesis and Biological Evaluation of Jerantinine E
Reto Frei, Davide Staedler, Aruna Raja, Raimo Franke, Florenz Sasse, Sandrine Gerber-Lemaire and Jerome Waser
Angew. Chem., Int. Ed. 2013, 52, 13373-13376. (DOI: 10.1002/anie.201305533Green Access

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
Yifan Li and Jerome Waser
Beilstein J. Org. Chem. 2013, 9, 1763-1767. (DOI: 10.3762/bjoc.9.204) Open Access!

Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition
Florian de Nanteuil and Jerome Waser
Angew. Chem., Int. Ed. 2013, 52, 9009–9013. (DOI: 10.1002/anie.201303803Green Access

Catalytic Friedel–Crafts Reaction of Aminocyclopropanes
Florian de Nanteuil, Joachim Loup and Jerome Waser
Org. Lett. 2013, 15, 3738-3741. (DOI: 10.1021/ol401616aGreen Access

A Highly Chemoselective and Practical Alkynylation of Thiols
Reto Frei and Jerome Waser
J. Am. Chem. Soc. 2013, 135, 9620-9623. (DOI: 10.1021/ja4044196Green Access

Azidation of Beta-Keto Esters and Silyl Enol Ethers with a Benziodoxole Reagent
Maria Victoria Vita and Jerome Waser
Org. Lett. 2013, 15, 3246-3249. (DOI: 10.1021/ol401229vGreen Access

Ethynylbenziodoxolones (EBX) as Reagents for the Ethynylation of Stabilized Enolates
Davinia Fernández González, Jonathan P. Brand, Régis Mondière and Jerome Waser
Adv. Synth. Catal. 2013, 355, 1631-1639. (DOI: 10.1002/adsc.201300266Green Access

Gold-Catalyzed Regioselective Synthesis of 2- and 3-Alkynyl Furans
Yifan Li, Jonathan P. Brand and Jerome Waser
Angew. Chem., Int. Ed. 2013, 52, 6743-6747. (DOI: 10.1002/anie.201302210Green Access

Pd(0)-Catalyzed Alkene Oxy- and Aminoalkynylation with Aliphatic Bromoacetylenes
Stefano Nicolai, Raha Sedigh-Zadeh , and Jerome Waser
J. Org. Chem. 2013, 78, 3783-3801. (DOI: 10.1021/jo400254qGreen Access

C2-Selective Direct Alkynylation of Indoles
Gergely L. Tolnai , Stephanie Ganss, Jonathan P. Brand and Jerome Waser
Org. Lett. 2013, 15, 112-115. (DOI: 10.1021/ol3031389Green Access

2012

Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1λ3,2-benziodoxol-3(1H)-one and Alkynylation of Indoles, Thiophenes, and Anilines
Jonathan P. Brand and Jerome Waser
Synthesis 2012, 44, 1155-1158. (DOI: 10.1055/s-0031-1290589Green Access

Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism
Jonathan P. Brand, Clara Chevalley, Rosario Scopelliti and Jerome Waser
Chem. Eur. J. 2012, 18, 5655-5666. (DOI:10.1002/chem.201200200 Green Access

Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones
Fides Benfatti, Florian de Nanteuil and Jerome Waser
Chem. Eur. J. 2012, 18, 4844-4849. (DOI:10.1002/chem.201103971 Green Access

Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines.
Jonathan P. Brand and Jerome Waser
Org. Lett. 2012, 14, 744-747. (DOI: 10.1021/ol203289v Green Access

Iron-Catalyzed [3 + 2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans.
Fides Benfatti, Florian de Nanteuil and Jerome Waser
Org. Lett. 2012, 14, 386-389. (DOI: 10.1021/ol203144v Green Access

2011

Formal Homo-Nazarov and Other Cyclization Reactions of Activated Cyclopropanes.
Filippo De Simone, Tanguy Saget, Fides Benfatti, Sofia Almeida and Jerome Waser
Chem. Eur. J. 2011, 17, 14527-14538. (DOI: 10.1002/chem.201102583 Green Access

Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines .
Stefano Nicolai and Jerome Waser
Org. Lett. 2011, 13, 6324-6327. (DOI: 10.1021/ol2029383 Green Access

Catalytic [3+2] Annulation of Aminocyclopropanes for the Enantiospecific Synthesis of Cyclopentylamines.
Florian de Nanteuil and Jerome Waser
Angew. Chem., Int. Ed. 2011, 50, 12075-12079. (DOI: 10.1002/anie.201106255Green Access

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.
Jonathan P. Brand, Clara Chevalley and Jerome Waser
Beilstein J. Org. Chem. 2011, 7, 565–569. DOI:10.3762/bjoc.7.65 Open Access!

A Palladium-Catalyzed Aminoalkynylation Strategy towards Bicyclic Heterocycles: Synthesis of Trachelanthamidine.
Stefano Nicolai, Cyril Piemontesi and Jerome Waser
Angew. Chem., Int. Ed. 2011, 50, 4680-4683.   DOI: 10.1002/anie.201100718    Green Access

2010

Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-Ethynyl-Benziodoxolone with Gold and Brønsted Acids.
Jonathan P. Brand and Jerome Waser
Angew. Chem., Int. Ed. 2010, 49, 7304-7307.   DOI: 10.1002/anie.201003179    Green Access

Ethynyl-1,2-benziodoxol-3-(1H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto-, Cyano- and Nitro- Esters.
Davinia Fernandez Gonzalez, Jonathan P. Brand and Jerome Waser
Chem. Eur. J. 2010, 16, 9457-9461.   DOI: 10.1002/chem.201001539   Green Access

Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine
Filippo De Simone, Juerg Gertsch and Jerome Waser
Angew. Chem., Int. Ed. 2010, 49, 5767-5770.   DOI: 10.1002/anie.201001853    Green Access

Synthesis of Chiral Bifunctional (Thio)urea N-Heterocyclic Carbenes
Jonathan B. Brand, Jose Ignacio Osuna Siles and Jerome Waser
Synlett 2010, 881-884.   DOI: 10.1055/s-0029-1219543   Green Access

Pd-Catalyzed Intramolecular Oxyalkynylation of Alkenes with Hypervalent Iodine
Stefano Nicolai, Stephane Erard, Davinia Fernandez-Gonzalez and Jerome Waser
Org. Lett. 2010, 12, 384-387.   DOI: 10.1021/ol9027286    Green Access

2009

Direct Alkynylation of Pyrrole and Indole Heterocycles
Jonathan P. Brand, Julie Charpentier and Jerome Waser
Angew. Chem., Int. Ed. 2009, 48, 9346-9349.   DOI: 10.1002/anie.200905419    Green Access

Catalytic Formal Homo-Nazarov Cyclization
Filippo De Simone, Julien Andres, Riccardo Torosantucci and Jerome Waser
Org. Lett. 2009, 11, 1023-1026.   DOI: 10.1021/ol802970g    Green Access

review-articles

2018

Hypervalent Halogen Compounds: Alkynylations and Vinylations
Durga Prasad Hari, Stefano Nicolai and Jerome Waser
PATAI’S Chemistry of Functional Groups 2018, John Wiley & Sons, Ltd. (DOI: 10.1002/9780470682531.pat095)

2017

Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents
Franck Le Vaillant and Jerome Waser
Chimia 2017, 71, 226-230. (DOI: 10.2533/chimia.2017.226)

In situ tether formation from amines and alcohols enabling highly selective Tsuji–Trost allylation and olefin functionalization
Ugo Orcel and Jerome Waser
Chem. Sci. 2017, 8, 32-39. (DOI: 10.1039/C6SC04366F )

2016

Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis
Jerome Waser
Synlett 2016, 27, 2761-2773. (DOI: 10.1055/s-0036-1589409)

Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation
Yifan Li, Durga Prasad Hari, Maria Victoria Vita and Jerome Waser
Angew. Chem., Int. Ed. 2016, 55, 4436–4454. (DOI: 10.1002/anie.201509073Green Access

2015

Alkynylation with Hypervalent Iodine Reagents
Jerome Waser
Top. Curr. Chem. 2015. (DOI: 10.1007/128_2015_660Green Access

Cyclic Hypervalent Iodine Reagents and Iron Catalysts: The Winning Team for Late-Stage C-H Azidation
Maria Victoria Vita and Jerome Waser
Angew. Chem., Int. Ed. 2015, 54, 5290-5292. (DOI: 10.1002/anie.201501666Green Access

2014

Taming Hypervalent Bonds and Strained Rings for Catalysis and Synthesis.
Florian de Nanteuil, Yifan Li, Maria Victoria Vita, Reto Frei, Eloisa Serrano, Sophie Racine and Jerome Waser
Chimia 2014, 68, 516-521. DOI: 10.2533/chimia.2014.516 . Green Access

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes.
Florian de Nanteuil, Filippo De Simone, Reto Frei, Fides Benfatti, Eloisa Serrano and Jerome Waser
Chem. Commun. 2014, 50, 10912-10928. DOI: 10.1039/C4CC03194F . Green Access

2013

Gold-Catalyzed Alkynylation: Acetylene-Transfer instead of Functionalization.
Jonathan P. Brand, Yifan Li and Jerome Waser
Israel J. Chem. 2013, 53, 901-910. DOI:10.1002/ijch.201300044. Green Access

7. Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions that Generate a C–N or C–O Bond.
Jerome Waser
Topics in Heterocyclic Chemistry, Vol. 32 Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate one or More Carbon Heteroatom Bonds , Ed. J. P. Wolfe, Springer 2013, p. 225-270. Link Green Access

2012

SILYL ETHYNYL BENZIODOXOLONE REAGENTS.
Davinia Fernández González, Stefano Nicolai, and Jérôme Waser
Electronic Encyclopedia of Reagents for Organic Synthesis , John Wiley & Sons, 2012. DOI:10.1002/047084289X.rn01503.

Electrophilic alkynylation: the dark side of acetylene chemistry.
Jonathan P. Brand and Jerome Waser
Chem. Soc. Rev. 2012, 41, 4165-4179. DOI:10.1039/C2CS35034C. Green Access

Asymmetric Organocatalysis Meets Hypervalent Iodine Chemistry for the α-Functionalization of Carbonyl Compounds.
Davinia Fernández González,Fides Benfatti, and Jérôme Waser
ChemCatChem 2012, 4, 955-958. DOI:10.1002/cctc.201200116. Green Access

2011

Cyclopropanes and Hypervalent Iodine Reagents: High Energy Compounds for Applications in Synthesis and Catalysis.
Davinia Fernandez Gonzalez, Filippo De Simone, Jonathan Brand, Stefano Nicolai and Jerome Waser
Chimia 2011, 65, 649-651.   DOI:10.2533/chimia.2011.649.    Green Access

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis
Filippo De Simone and Jerome Waser
Synlett 2011,  589-593.   DOI:10.1055/s-0030-1259553.    Green Access

Benziodoxole-Based Hypervalent Iodine Reagents for Atom-Transfer Reactions
Jonathan P. Brand,  Davinia Fernandez Gonzalez,  Stefano Nicolai and Jerome Waser
Chem. Commun. 2011, 47, 102-115.   DOI:10.1039/C0CC02265A.    Green Access

2009

Cyclization and Cycloaddition Reactions of Cyclopropyl Carbonyls and Imines
Filippo De Simone and Jerome Waser
Synthesis 2009, 3353-3374.   DOI: 10.1055/s-0029-1216998    Green Access

Cyclization of Cyclopropyl Carbonyls and the Homo Nazarov Reaction
Filippo De Simone and Jerome Waser
Chimia 2009, 63, 162-167.   DOI: 10.2533/chimia.2009.162    Green Access