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Title: Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes

Abstract

An efficient approach for synthesizing congested deuterium-labeled arenes via cascade alkylation and deuteration with aryl iodides has been disclosed. Here, we found that the adoption of sodium formate-$d$ as a deuterium source is the key for achieving high deuterium incorporation >98%.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [1];  [2]; ORCiD logo [1];  [1]
  1. Nanjing Tech. Univ. Nanjing (China)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC); National Natural Science Foundation of China (NSFC)
OSTI Identifier:
1546519
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 55; Journal Issue: 59; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, and Liu, Xiang. Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes. United States: N. p., 2019. Web. doi:10.1039/C9CC03988K.
Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, & Liu, Xiang. Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes. United States. https://doi.org/10.1039/C9CC03988K
Guo, Lei, Xu, Chen, Wu, Ding-Chuan, Hu, Guang-Qi, Zhang, Hong-Hai, Hong, Kunlun, Chen, Su, and Liu, Xiang. Tue . "Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes". United States. https://doi.org/10.1039/C9CC03988K. https://www.osti.gov/servlets/purl/1546519.
@article{osti_1546519,
title = {Cascade alkylation and deuteration with aryl iodides via Pd/norbornene catalysis: an efficient method for the synthesis of congested deuterium-labeled arenes},
author = {Guo, Lei and Xu, Chen and Wu, Ding-Chuan and Hu, Guang-Qi and Zhang, Hong-Hai and Hong, Kunlun and Chen, Su and Liu, Xiang},
abstractNote = {An efficient approach for synthesizing congested deuterium-labeled arenes via cascade alkylation and deuteration with aryl iodides has been disclosed. Here, we found that the adoption of sodium formate-$d$ as a deuterium source is the key for achieving high deuterium incorporation >98%.},
doi = {10.1039/C9CC03988K},
journal = {ChemComm},
number = 59,
volume = 55,
place = {United States},
year = {2019},
month = {6}
}

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Works referenced in this record:

Reagent-Enabled ortho -Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis
journal, October 2016


Alkylating Reagents Employed in Catellani-Type Reactions
journal, October 2018

  • Liu, Ze-Shui; Gao, Qianwen; Cheng, Hong-Gang
  • Chemistry - A European Journal, Vol. 24, Issue 58
  • DOI: 10.1002/chem.201802818

Cryptocatalytic 1,2-Alkene Migration in a σ-Alkyl Palladium Diene Complex
journal, July 2009

  • Evans, Louise A.; Fey, Natalie; Lloyd-Jones, Guy C.
  • Angewandte Chemie International Edition, Vol. 48, Issue 34
  • DOI: 10.1002/anie.200901468

Ligand-enabled meta-C–H activation using a transient mediator
journal, March 2015

  • Wang, Xiao-Chen; Gong, Wei; Fang, Li-Zhen
  • Nature, Vol. 519, Issue 7543
  • DOI: 10.1038/nature14214

Palladium-Catalyzed Reductive ortho -Arylation: Evidence for the Decomposition of 1,2-Dimethoxyethane and Subsequent Arylpalladium(II) Reduction
journal, November 2010

  • Martins, Andrew; Candito, David A.; Lautens, Mark
  • Organic Letters, Vol. 12, Issue 22
  • DOI: 10.1021/ol1019037

Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes
journal, June 2017

  • Kerr, William J.; Reid, Marc; Tuttle, Tell
  • Angewandte Chemie International Edition, Vol. 56, Issue 27
  • DOI: 10.1002/anie.201702997

Selective, Ambient-Temperature C-4 Deuteration of Pyrazole Derivatives by D 2 O
journal, January 2018


Palladium-Catalyzed meta -C–H Functionalization of Masked Aromatic Aldehydes
journal, July 2018


A New Route to Fused Aromatic Compounds by Using a Palladium-Catalyzed Alkylation - Alkenylation Sequence
journal, March 2000


Complete Replacement of H 2 by D 2 via Pd/C-Catalyzed H/D Exchange Reaction
journal, September 2004

  • Sajiki, Hironao; Kurita, Takanori; Esaki, Hiroyoshi
  • Organic Letters, Vol. 6, Issue 20
  • DOI: 10.1021/ol048591b

Afterglow Organic Light-Emitting Diode
journal, November 2015


Aryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation
journal, January 2007

  • Alberico, Dino; Scott, Mark E.; Lautens, Mark
  • Chemical Reviews, Vol. 107, Issue 1
  • DOI: 10.1021/cr0509760

Radical Deuteration with D 2 O: Catalysis and Mechanistic Insights
journal, December 2017

  • Soulard, Valentin; Villa, Giorgio; Vollmar, Denis Patrick
  • Journal of the American Chemical Society, Vol. 140, Issue 1
  • DOI: 10.1021/jacs.7b12105

Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation
journal, August 2011

  • Jiao, Lei; Bach, Thorsten
  • Journal of the American Chemical Society, Vol. 133, Issue 33
  • DOI: 10.1021/ja2055066

Isotope effect in spin response of π-conjugated polymer films and devices
journal, February 2010

  • Nguyen, Tho D.; Hukic-Markosian, Golda; Wang, Fujian
  • Nature Materials, Vol. 9, Issue 4
  • DOI: 10.1038/nmat2633

Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex
journal, January 2019

  • Zhou, Zhao-Zhao; Zhao, Jia-Hui; Gou, Xue-Ya
  • Organic Chemistry Frontiers, Vol. 6, Issue 10
  • DOI: 10.1039/C9QO00240E

Palladium-Catalyzed Alkylation−Hydride Reduction Sequence:  Synthesis of Meta-Substituted Arenes
journal, September 2005

  • Wilhelm, Thorsten; Lautens, Mark
  • Organic Letters, Vol. 7, Issue 18
  • DOI: 10.1021/ol051628n

Structural absorption by barbule microstructures of super black bird of paradise feathers
journal, January 2018


Using Deuterium in Drug Discovery: Leaving the Label in the Drug
journal, December 2013

  • Gant, Thomas G.
  • Journal of Medicinal Chemistry, Vol. 57, Issue 9
  • DOI: 10.1021/jm4007998

Cleavage of the C(O)–S Bond of Thioesters by Palladium/Norbornene/Copper Cooperative Catalysis: An Efficient Synthesis of 2-(Arylthio)aryl Ketones
journal, June 2016

  • Sun, Fenggang; Li, Miao; He, Congfa
  • Journal of the American Chemical Society, Vol. 138, Issue 24
  • DOI: 10.1021/jacs.6b02495

First deuterated drug approved
journal, June 2017


Palladium−Arene Interactions in Catalytic Intermediates:  An Experimental and Theoretical Investigation of the Soft Rearrangement between η 1 and η 2 Coordination Modes
journal, April 2002

  • Catellani, Marta; Mealli, Carlo; Motti, Elena
  • Journal of the American Chemical Society, Vol. 124, Issue 16
  • DOI: 10.1021/ja016587e

Ruthenium-catalyzed hydrogen isotope exchange of C(sp 3 )–H bonds directed by a sulfur atom
journal, January 2018

  • Gao, Longhui; Perato, Serge; Garcia-Argote, Sébastien
  • Chemical Communications, Vol. 54, Issue 24
  • DOI: 10.1039/C8CC00653A

Highly Selective Directed Iridium-Catalyzed Hydrogen Isotope Exchange Reactions of Aliphatic Amides
journal, May 2018

  • Valero, Mégane; Weck, Remo; Güssregen, Stefan
  • Angewandte Chemie International Edition, Vol. 57, Issue 27
  • DOI: 10.1002/anie.201804010

General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides
journal, August 2018

  • Wang, Xin; Zhu, Ming-Hui; Schuman, David P.
  • Journal of the American Chemical Society, Vol. 140, Issue 35
  • DOI: 10.1021/jacs.8b07597

Ortho CH Acylation of Aryl Iodides by Palladium/Norbornene Catalysis
journal, September 2015

  • Dong, Zhe; Wang, Jianchun; Ren, Zhi
  • Angewandte Chemie International Edition, Vol. 54, Issue 43
  • DOI: 10.1002/anie.201506397

Synthesis of Deuterated Benzopyran Derivatives as Selective COX-2 Inhibitors with Improved Pharmacokinetic Properties
journal, August 2014

  • Zhang, Yanmei; Tortorella, Micky D.; Wang, Yican
  • ACS Medicinal Chemistry Letters, Vol. 5, Issue 10
  • DOI: 10.1021/ml500299q

A facile and general acid-catalyzed deuteration at methyl groups of N-heteroarylmethanes
journal, January 2017

  • Liu, Min; Chen, Xue; Chen, Tieqiao
  • Organic & Biomolecular Chemistry, Vol. 15, Issue 12
  • DOI: 10.1039/C7OB00062F

Selective deuteration of (hetero)aromatic compounds via deutero-decarboxylation of carboxylic acids
journal, January 2012

  • Grainger, Rachel; Nikmal, Arif; Cornella, Josep
  • Organic & Biomolecular Chemistry, Vol. 10, Issue 16
  • DOI: 10.1039/c2ob25157d

Enantioselective remote meta-C–H arylation and alkylation via a chiral transient mediator
journal, June 2018


Deuterodechlorination of Aryl/Heteroaryl Chlorides Catalyzed by a Palladium/Unsymmetrical NHC System
journal, September 2016

  • Kuriyama, Masami; Hamaguchi, Norihisa; Yano, Gemba
  • The Journal of Organic Chemistry, Vol. 81, Issue 19
  • DOI: 10.1021/acs.joc.6b01609

Epoxides as Alkylating Reagents for the Catellani Reaction
journal, February 2018

  • Cheng, Hong-Gang; Wu, Chenggui; Chen, Han
  • Angewandte Chemie International Edition, Vol. 57, Issue 13
  • DOI: 10.1002/anie.201800573

Efficient Route to Deuterated Aromatics by the Deamination of Anilines
journal, July 2016


Symmetrical and unsymmetrical 2,6-dialkyl-1,1′-biaryls by combined catalysis of aromatic alkylation via palladacycles and Suzuki-type coupling
journal, January 2000

  • Catellani, Marta; Motti, Elena; Minari, Monica
  • Chemical Communications, Issue 2
  • DOI: 10.1039/a909099a

Catalytic selective deuteration of halo(hetero)arenes
journal, January 2016

  • Janni, Manojkumar; Peruncheralathan, S.
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 11
  • DOI: 10.1039/C6OB00193A

Palladium-Catalyzed Heteroarylation and Concomitant ortho -Alkylation of Aryl Iodides
journal, September 2015

  • Lei, Chuanhu; Jin, Xiaojia; Zhou, Jianrong Steve
  • Angewandte Chemie International Edition, Vol. 54, Issue 45
  • DOI: 10.1002/anie.201507128

Pd(II)-Catalyzed Catellani-Type Domino Reaction Utilizing Arylboronic Acids as Substrates
journal, March 2018


Metal–Organic Cooperative Catalysis in C–H and C–C Bond Activation
journal, January 2017


Pd-Catalyzed para -selective C–H difluoromethylation of aromatic carbonyls
journal, January 2019

  • Mao, Yang-Jie; Wang, Bing-Xin; Wu, Qiu-Zi
  • Chemical Communications, Vol. 55, Issue 14
  • DOI: 10.1039/C8CC09129C

Modular C–H Functionalization Cascade of Aryl Iodides
journal, March 2015

  • Shi, Hang; Babinski, David J.; Ritter, Tobias
  • Journal of the American Chemical Society, Vol. 137, Issue 11
  • DOI: 10.1021/jacs.5b01082

Iridium-Catalyzed Csp 3 –H Activation for Mild and Selective Hydrogen Isotope Exchange
journal, September 2018


Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design
journal, April 2011

  • Meanwell, Nicholas A.
  • Journal of Medicinal Chemistry, Vol. 54, Issue 8
  • DOI: 10.1021/jm1013693

A para -C-H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents : A
journal, November 2018

  • Tian, Chao; Yao, Xu; Ji, Weizhe
  • European Journal of Organic Chemistry, Vol. 2018, Issue 43
  • DOI: 10.1002/ejoc.201801058

Kinetic Isotope Effects in Asymmetric Reactions
journal, July 2010

  • Giagou, Thomas; Meyer, Matthew P.
  • Chemistry - A European Journal, Vol. 16, Issue 35
  • DOI: 10.1002/chem.201001018

Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates
journal, December 2016

  • Kuriyama, Masami; Kujirada, Shota; Tsukuda, Kotaro
  • Advanced Synthesis & Catalysis, Vol. 359, Issue 6
  • DOI: 10.1002/adsc.201601105

Simple Amine-Directed Meta-Selective C–H Arylation via Pd/Norbornene Catalysis
journal, April 2015

  • Dong, Zhe; Wang, Jianchun; Dong, Guangbin
  • Journal of the American Chemical Society, Vol. 137, Issue 18
  • DOI: 10.1021/jacs.5b02809

Hydrogen/Deuterium (H/D) Exchange Catalysis in Alkanes
journal, January 2018


Pd( ii )-Catalyzed decarboxylative meta -C–H difluoromethylation
journal, January 2019

  • Zhao, Huaxin; Ma, Guobin; Xie, Xiaojuan
  • Chemical Communications, Vol. 55, Issue 27
  • DOI: 10.1039/C9CC00984A

Metal-catalysed hydrogen isotope exchange labelling: a brief overview
journal, September 2010

  • Lockley, William J. S.; Heys, J. Richard
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 53, Issue 11-12
  • DOI: 10.1002/jlcr.1851

Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps
journal, November 2008

  • Catellani, Marta; Motti, Elena; Della Ca’, Nicola
  • Accounts of Chemical Research, Vol. 41, Issue 11
  • DOI: 10.1021/ar800040u

Of the Ortho Effect in Palladium/Norbornene-Catalyzed Reactions: A Theoretical Investigation
journal, June 2011

  • Maestri, Giovanni; Motti, Elena; Della Ca’, Nicola
  • Journal of the American Chemical Society, Vol. 133, Issue 22
  • DOI: 10.1021/ja110988p

Pd- and Pt-catalyzed H/D exchange methods and their application for internal MS standard preparation from a Sanofi-Aventis perspective
journal, September 2010

  • Atzrodt, Jens; Derdau, Volker
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 53, Issue 11-12
  • DOI: 10.1002/jlcr.1818

Development of a QuEChERS-Based Stable-Isotope Dilution LC-MS/MS Method To Quantitate Ferulic Acid and Its Main Microbial and Hepatic Metabolites in Milk
journal, November 2016

  • Waterstraat, Martin; Hildebrand, Andreas; Rosler, Margit
  • Journal of Agricultural and Food Chemistry, Vol. 64, Issue 45
  • DOI: 10.1021/acs.jafc.6b03318

Mechanistic Analysis of Azine N -Oxide Direct Arylation: Evidence for a Critical Role of Acetate in the Pd(OAc) 2 Precatalyst
journal, December 2010

  • Sun, Ho-Yan; Gorelsky, Serge I.; Stuart, David R.
  • The Journal of Organic Chemistry, Vol. 75, Issue 23
  • DOI: 10.1021/jo101821r

Methyl Substitution of a Rexinoid Agonist Improves Potency and Reveals Site of Lipid Toxicity
journal, June 2014

  • Atigadda, Venkatram R.; Xia, Gang; Desphande, Anil
  • Journal of Medicinal Chemistry, Vol. 57, Issue 12
  • DOI: 10.1021/jm5004792

Design, synthesis and evaluation of novel N-phenylbutanamide derivatives as KCNQ openers for the treatment of epilepsy
journal, September 2018

  • Yang, Shaoning; Lu, Dingqiang; Ouyang, Pingkai
  • Bioorganic & Medicinal Chemistry Letters, Vol. 28, Issue 17
  • DOI: 10.1016/j.bmcl.2018.05.019

Site-Selective Nickel-Catalyzed Hydrogen Isotope Exchange in N -Heterocycles and Its Application to the Tritiation of Pharmaceuticals
journal, September 2018


A New Reaction Sequence Involving Palladium-Catalyzed Unsymmetrical Aryl Coupling
journal, January 2004

  • Faccini, Fiorenza; Motti, Elena; Catellani, Marta
  • Journal of the American Chemical Society, Vol. 126, Issue 1
  • DOI: 10.1021/ja039043g

Palladium-Catalyzed Catellani ortho -Acylation Reaction: An Efficient and Regiospecific Synthesis of Diaryl Ketones
journal, September 2015

  • Huang, Yunze; Zhu, Rui; Zhao, Kun
  • Angewandte Chemie International Edition, Vol. 54, Issue 43
  • DOI: 10.1002/anie.201506446

A General Strategy for Site-Selective Incorporation of Deuterium and Tritium into Pyridines, Diazines, and Pharmaceuticals
journal, February 2018

  • Koniarczyk, J. Luke; Hesk, David; Overgard, Alix
  • Journal of the American Chemical Society, Vol. 140, Issue 6
  • DOI: 10.1021/jacs.7b11710

Picomolar Inhibitors of HIV-1 Reverse Transcriptase: Design and Crystallography of Naphthyl Phenyl Ethers
journal, September 2014

  • Lee, Won-Gil; Frey, Kathleen M.; Gallardo-Macias, Ricardo
  • ACS Medicinal Chemistry Letters, Vol. 5, Issue 11
  • DOI: 10.1021/ml5003713

Palladium-Catalyzed ortho -Selective CH Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles
journal, November 2013

  • Ma, Sandy; Villa, Giorgio; Thuy-Boun, Peter S.
  • Angewandte Chemie International Edition, Vol. 53, Issue 3
  • DOI: 10.1002/anie.201305388

Ruthenium( ii )-catalyzed selective C–H difluoroalkylation of aniline derivatives with pyrimidyl auxiliaries
journal, January 2018

  • Wang, Xin-Gang; Li, Yuke; Zhang, Lu-Lu
  • Chemical Communications, Vol. 54, Issue 68
  • DOI: 10.1039/C8CC05067H

Palladium-Catalyzed/Norbornene-Mediated ortho -Amination/ N -Tosylhydrazone Insertion Reaction: An Approach to the Synthesis of ortho -Aminated Vinylarenes
journal, July 2014

  • Zhou, Ping-Xin; Ye, Yu-Ying; Ma, Jun-Wei
  • The Journal of Organic Chemistry, Vol. 79, Issue 14
  • DOI: 10.1021/jo501125b

Stereochemistry and Mechanism of the Brønsted Acid Catalyzed Intramolecular Hydrofunctionalization of an Unactivated Cyclic Alkene
journal, April 2011

  • McKinney Brooner, Rachel E.; Widenhoefer, Ross A.
  • Chemistry – A European Journal, Vol. 17, Issue 22
  • DOI: 10.1002/chem.201003128

C−H Functionalisation for Hydrogen Isotope Exchange
journal, February 2018

  • Atzrodt, Jens; Derdau, Volker; Kerr, William J.
  • Angewandte Chemie International Edition, Vol. 57, Issue 12
  • DOI: 10.1002/anie.201708903

On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes
journal, March 2012

  • Simmons, Eric M.; Hartwig, John F.
  • Angewandte Chemie International Edition, Vol. 51, Issue 13
  • DOI: 10.1002/anie.201107334

Ortho vs Ipso : Site-Selective Pd and Norbornene-Catalyzed Arene C–H Amination Using Aryl Halides
journal, November 2013

  • Dong, Zhe; Dong, Guangbin
  • Journal of the American Chemical Society, Vol. 135, Issue 49
  • DOI: 10.1021/ja410823e

Modular ipso / ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis
journal, June 2018

  • Dong, Zhe; Lu, Gang; Wang, Jianchun
  • Journal of the American Chemical Society, Vol. 140, Issue 27
  • DOI: 10.1021/jacs.8b04153

The ruthenium-catalysed selective synthesis of mono-deuterated terminal alkynes
journal, January 2016

  • Chatterjee, Basujit; Gunanathan, Chidambaram
  • Chemical Communications, Vol. 52, Issue 24
  • DOI: 10.1039/C6CC01401A

Deoxygenative Deuteration of Carboxylic Acids with D 2 O
journal, November 2018

  • Zhang, Muliang; Yuan, Xiang-Ai; Zhu, Chengjian
  • Angewandte Chemie International Edition, Vol. 58, Issue 1
  • DOI: 10.1002/anie.201811522

Ligand Promoted meta -C–H Chlorination of Anilines and Phenols
journal, November 2016

  • Shi, Hang; Wang, Peng; Suzuki, Shin
  • Journal of the American Chemical Society, Vol. 138, Issue 45
  • DOI: 10.1021/jacs.6b11055

Effect of Deuterium Substitution on the Physical Properties of Polymer Melts and Blends
journal, May 2010

  • White, Ronald P.; Lipson, Jane E. G.; Higgins, Julia S.
  • Macromolecules, Vol. 43, Issue 9
  • DOI: 10.1021/ma902707u

Lipidomics Reveals Dramatic Physiological Kinetic Isotope Effects during the Enzymatic Oxygenation of Polyunsaturated Fatty Acids Ex Vivo
journal, December 2017

  • Navratil, Aaron R.; Shchepinov, Mikhail S.; Dennis, Edward A.
  • Journal of the American Chemical Society, Vol. 140, Issue 1
  • DOI: 10.1021/jacs.7b09493

Palladium-catalyzed Br/D exchange of arenes: selective deuterium incorporation with versatile functional group tolerance and high efficiency
journal, January 2015

  • Zhang, Hong-Hai; Bonnesen, Peter V.; Hong, Kunlun
  • Organic Chemistry Frontiers, Vol. 2, Issue 9
  • DOI: 10.1039/C5QO00181A

Palladium/Norbornene Cooperative Catalysis
journal, April 2019


Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides
journal, February 2016


Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences
journal, January 2018

  • Atzrodt, Jens; Derdau, Volker; Kerr, William J.
  • Angewandte Chemie International Edition, Vol. 57, Issue 7
  • DOI: 10.1002/anie.201704146

C5-selective trifluoromethylation of 8-amino quinolines via photoredox catalysis
journal, March 2019


The Renaissance of H/D Exchange
journal, October 2007

  • Atzrodt, Jens; Derdau, Volker; Fey, Thorsten
  • Angewandte Chemie International Edition, Vol. 46, Issue 41
  • DOI: 10.1002/anie.200700039

Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds
journal, November 2017


Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C–H Bond Activation
journal, June 2016


The effect of isotopic substitution on the chirality of a self-assembled helix
journal, October 2010

  • Cantekin, Seda; Balkenende, Diederik W. R.; Smulders, Maarten M. J.
  • Nature Chemistry, Vol. 3, Issue 1
  • DOI: 10.1038/nchem.889

Heavy drugs draw heavy interest from pharma backers
journal, June 2013


The Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction
journal, May 2018

  • Chen, Shuqing; Liu, Ze-Shui; Yang, Tao
  • Angewandte Chemie International Edition, Vol. 57, Issue 24
  • DOI: 10.1002/anie.201803865

Cryptocatalytic 1,2-Alkene Migration in a σ-Alkyl Palladium Diene Complex
journal, July 2009

  • Evans, Louise A.; Fey, Natalie; Lloyd-Jones, Guy C.
  • Angewandte Chemie, Vol. 121, Issue 34
  • DOI: 10.1002/ange.200901468

Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes
journal, June 2017

  • Kerr, William J.; Reid, Marc; Tuttle, Tell
  • Angewandte Chemie, Vol. 129, Issue 27
  • DOI: 10.1002/ange.201702997

Epoxides as Alkylating Reagents for the Catellani Reaction
journal, February 2018


Deoxygenative Deuteration of Carboxylic Acids with D 2 O
journal, November 2018

  • Zhang, Muliang; Yuan, Xiang-Ai; Zhu, Chengjian
  • Angewandte Chemie, Vol. 131, Issue 1
  • DOI: 10.1002/ange.201811522

Palladium‐Catalyzed Heteroarylation and Concomitant ortho ‐Alkylation of Aryl Iodides
journal, September 2015

  • Lei, Chuanhu; Jin, Xiaojia; Zhou, Jianrong (Steve)
  • Angewandte Chemie, Vol. 127, Issue 45
  • DOI: 10.1002/ange.201507128

The Discovery of a Palladium(II)-Initiated Borono-Catellani Reaction
journal, May 2018


The Renaissance of H/D Exchange
journal, December 2007


Appetite-enhancing effects of inhaling cinnamon, clove, and fennel essential oils containing phenylpropanoid analogues
journal, June 2020


A New Reaction Sequence Involving Palladium-Catalyzed Unsymmetrical Aryl Coupling.
journal, June 2004


Aryl—Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation
journal, May 2007


Palladium-Catalyzed Alkylation—Hydride Reduction Sequence: Synthesis of meta-Substituted Arenes.
journal, January 2006


Palladium-Catalyzed ortho -Selective CH Deuteration of Arenes: Evidence for Superior Reactivity of Weakly Coordinated Palladacycles
journal, November 2013

  • Ma, Sandy; Villa, Giorgio; Thuy-Boun, Peter S.
  • Angewandte Chemie, Vol. 126, Issue 3
  • DOI: 10.1002/ange.201305388

Highly Selective Directed Iridium‐Catalyzed Hydrogen Isotope Exchange Reactions of Aliphatic Amides
journal, July 2018

  • Valero, Mégane; Weck, Remo; Güssregen, Stefan
  • Angewandte Chemie, Vol. 130, Issue 27
  • DOI: 10.1002/ange.201804010