Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Zhao Q, Rahman M, Zhou T, Yang S, Lalancette R, Szostak R, Szostak M. Wingtip-Flexible N-Heterocyclic Carbenes: Unsymmetrical Connection between IMes and IPr. Angew Chem Int Ed Engl. 2024 Feb 19;63(8):e202318703. doi: 10.1002/anie.202318703. Epub 2024 Jan 16. PubMed PMID: 38135660; PubMed Central PMCID: PMC10922840.
Gao P, Rahman MM, Zamalloa A, Feliciano J, Szostak M. Classes of Amides that Undergo Selective N-C Amide Bond Activation: The Emergence of Ground-State Destabilization. J Org Chem. 2023 Oct 6;88(19):13371-13391. doi: 10.1021/acs.joc.2c01094. Epub 2022 Sep 2. Review. PubMed PMID: 36054817.
Podchorodecka P, Dziuk B, Szostak R, Szostak M, Bisz E. IPr*(Oxa) - a new class of sterically-hindered, wingtip-flexible N,C-chelating oxazole-donor N-heterocyclic carbene ligands. Dalton Trans. 2023 Oct 3;52(38):13608-13617. doi: 10.1039/d3dt02255b. PubMed PMID: 37698540.
Zhang W, Ma J, Zhou F, Szostak M, Liu C. Carboxylic Acids as Double Aryl Group Donors for Biaryl Synthesis. Organic chemistry frontiers : an international journal of organic chemistry. 2023 October; 10(22):5698-5704. doi: 10.1039/D3QO01246H.
Rahman M, Gao P, Zhao Q, Lalancette R, Szostak R, Szostak M. [Au(Np(#))Cl]: Highly Reactive and Broadly Applicable Au(I)─NHC Catalysts for Alkyne π-Activation Reactions. Catal Sci Technol. 2023 Sep 7;13(17):5131-5139. doi: 10.1039/d3cy00717k. Epub 2023 Jul 26. PubMed PMID: 38464950; PubMed Central PMCID: PMC10923537.
Zhu X, Wan K, Zhang J, Zhao H, He Y, Ma Y, Yang X, Szostak M. Esterification of Thioamides via Selective N-C(S) Cleavage under Mild Conditions. Org Lett. 2023 Aug 25;25(33):6149-6154. doi: 10.1021/acs.orglett.3c02238. Epub 2023 Aug 14. PubMed PMID: 37578346.
Yang S, Yu X, Liu Y, Tomasini M, Caporaso L, Poater A, Cavallo L, Cazin CSJ, Nolan SP, Szostak M. Suzuki-Miyaura Cross-Coupling of Amides by N-C Cleavage Mediated by Air-Stable, Well-Defined [Pd(NHC)(sulfide)Cl(2)] Catalysts: Reaction Development, Scope, and Mechanism. J Org Chem. 2023 Aug 4;88(15):10858-10868. doi: 10.1021/acs.joc.3c00912. Epub 2023 Jul 19. PubMed PMID: 37467445.
Rahman MM, Zhao Q, Meng G, Lalancette R, Szostak R, Szostak M. [IPr(#)-PEPPSI]: A Well-Defined, Highly Hindered and Broadly Applicable Pd(II)-NHC (NHC = N-Heterocyclic Carbene) Precatalyst for Cross-Coupling Reactions. Molecules. 2023 Aug 2;28(15). doi: 10.3390/molecules28155833. PubMed PMID: 37570803; PubMed Central PMCID: PMC10421006.
Ji H, Cao H, Wang G, Xing F, Szostak M, Liu C. Predominant Intermolecular Decarbonylative Thioetherification of Carboxylic Acids Using Nickel Precatalysts. Organic chemistry frontiers : an international journal of organic chemistry. 2023 July; 10(17):4275-4281. doi: 10.1039/D3QO00744H.
Gao P, Szostak M. Hydration Reactions Catalyzed by Transition Metal-NHC (NHC = N-Heterocyclic Carbene) Complexes. Coord Chem Rev. 2023 Jun 15;485. doi: 10.1016/j.ccr.2023.215110. Epub 2023 Mar 30. PubMed PMID: 37064328; PubMed Central PMCID: PMC10104449.
Rahman MM, Meng G, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. ItOct (ItOctyl) - pushing the limits of ItBu: highly hindered electron-rich N-aliphatic N-heterocyclic carbenes. Chem Sci. 2023 May 17;14(19):5141-5147. doi: 10.1039/d3sc01006f. eCollection 2023 May 17. PubMed PMID: 37206400; PubMed Central PMCID: PMC10189875.
Hu Y, Gao Y, Ye J, Ma Z, Feng J, Liu X, Lei P, Szostak M. Suzuki-Miyaura Cross-Coupling of 2-Pyridyl Trimethylammonium Salts by N-C Activation Catalyzed by Air- and Moisture-Stable Pd-NHC Precatalysts: Application to the Discovery of Agrochemicals. Org Lett. 2023 May 5;25(17):2975-2980. doi: 10.1021/acs.orglett.3c00741. Epub 2023 Apr 20. PubMed PMID: 37079757.
Liu F, Anand L, Szostak M. Diversification of Indoles and Pyrroles by Molecular Editing: New Frontiers in Heterocycle-to-Heterocycle Transmutation. Chemistry. 2023 Apr 25;29(24):e202300096. doi: 10.1002/chem.202300096. Epub 2023 Mar 20. PubMed PMID: 36730110; PubMed Central PMCID: PMC10192006.
Liu X, Li X, Liu L, Huang T, Chen W, Szostak M, Chen T. Pd/Cu-Catalyzed Synthesis of Internal and Sila-Ynones by Direct Selective Acyl Sonogashira Cross-Coupling of Carboxylic Acids with Terminal Alkynes. ACS Catalysis. 2023 April; 13(9):5819–5827. doi: 10.1021/acscatal.2c06205.
Bie F, Liu X, Szostak M, Liu C. Decarbonylative Alkynylation of Aryl Anhydrides via Palladium Catalysis. J Org Chem. 2023 Apr 7;88(7):4442-4451. doi: 10.1021/acs.joc.2c03039. Epub 2023 Mar 10. PubMed PMID: 36896970.
Liu C, Xing YY, Zhou T, Chen T, Hong X, Szostak M. Carboxylic-Phosphoric Anhydrides as Direct Electrophiles for Decarbonylative Hirao Cross-Coupling of Carboxylic Acids: DFT Investigation of Mechanistic Pathway. Chem Asian J. 2023 Apr 3;18(7):e202201262. doi: 10.1002/asia.202201262. Epub 2023 Feb 20. PubMed PMID: 36748306.
Nan J, Ren X, Yan Q, Liu S, Wang J, Ma Y, Szostak M. Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles. Chem Sci. 2023 Mar 22;14(12):3338-3345. doi: 10.1039/d3sc00301a. eCollection 2023 Mar 22. PubMed PMID: 36970078; PubMed Central PMCID: PMC10034197.
Gao P, Xu J, Zhou T, Liu Y, Bisz E, Dziuk B, Lalancette R, Szostak R, Zhang D, Szostak M. L-Shaped Heterobidentate Imidazo[1,5-a]pyridin-3-ylidene (N,C)-Ligands for Oxidant-Free Au(I) /Au(III) Catalysis. Angew Chem Int Ed Engl. 2023 Mar 13;62(12):e202218427. doi: 10.1002/anie.202218427. Epub 2023 Feb 14. PubMed PMID: 36696514; PubMed Central PMCID: PMC9992098.
Liu C, Szostak M. Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling. SynOpen. 2023 March; 7(1):88-101. doi: 10.1055/a-2035-6733.
Liu C, Szostak M. Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling. SynOpen. 2023 Feb;7(1):88-101. doi: 10.1055/a-2035-6733. Epub 2023 Mar 6. PubMed PMID: 38037650; PubMed Central PMCID: PMC10686541.
Yang S, Yu X, Szostak M. Divergent Acyl and Decarbonylative Liebeskind-Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd-NHC (NHC = N-Heterocyclic Carbene) Catalysis. ACS Catal. 2023 Feb 3;13(3):1848-1855. doi: 10.1021/acscatal.2c05550. Epub 2023 Jan 17. PubMed PMID: 38037656; PubMed Central PMCID: PMC10686545.
Zhang J, Wang X, Liu J, Wang X, Yang X, Zhao Q, Ma Y, Fang R, Szostak M. Ruthenium(0)-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Organoboranes by Selective C–O cleavage. Organic Chemistry Frontiers. 2023 January; 10:1423-1428. doi: 10.1039/D3QO00042G.
Yang S, Zhou T, Yu X, Szostak M. Ag-NHC Complexes in the π-Activation of Alkynes. Molecules. 2023 Jan 18;28(3). doi: 10.3390/molecules28030950. Review. PubMed PMID: 36770617; PubMed Central PMCID: PMC9920927.
Yang S, Yu X, Szostak M. Divergent Acyl and Decarbonylative Liebeskind−Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd–NHC (NHC = N-Heterocyclic Carbene) Catalysis. ACS Catalysis. 2023 January; 13(3):1848–1855. doi: 10.1021/acscatal.2c05550.
Bisz E, Podchorodecka P, Li H, Ochędzan-Siodłak W, An J, Szostak M. Sequential Iron-Catalyzed C(sp(2))-C(sp(3)) Cross-Coupling of Chlorobenzamides/Chemoselective Amide Reduction and Reductive Deuteration to Benzylic Alcohols. Molecules. 2022 Dec 27;28(1). doi: 10.3390/molecules28010223. PubMed PMID: 36615417; PubMed Central PMCID: PMC9821805.
Yang S, Yu X, Poater A, Cavallo L, Cazin CSJ, Nolan SP, Szostak M. Buchwald-Hartwig Amination and C-S/S-H Metathesis of Aryl Sulfides by Selective C-S Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl](2) Precatalysts: Unified Mechanism for Activation of Inert C-S Bonds. Org Lett. 2022 Dec 23;24(50):9210-9215. doi: 10.1021/acs.orglett.2c03717. Epub 2022 Dec 8. PubMed PMID: 36480689.
Chu W, Zhou T, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. CAAC-IPr*: easily accessible, highly sterically-hindered cyclic (alkyl)(amino)carbenes. Chem Commun (Camb). 2022 Dec 6;58(97):13467-13470. doi: 10.1039/d2cc05668b. PubMed PMID: 36382995; PubMed Central PMCID: PMC9737351.
Zhang J, Li X, Li T, Wan K, Ma Y, Fang R, Szostak R, Szostak M. Copper(I)–Thiazol-2-ylidenes: Highly Reactive N-Heterocyclic Carbenes for the Hydroboration of Terminal and Internal Alkynes. Ligand Development, Synthetic Utility, and Mechanistic Studies. ACS Catalysis. 2022 November; 12(24):15323–15333. doi: 10.1021/acscatal.2c04668.
Kardela M, Halikowska-Tarasek K, Szostak M, Bisz E. Enhanced Activity of Bulky N-Heterocylic Carbenes in Nickel–NHC Catalyzed Kumada–Corriu Cross-Coupling of Aryl Tosylates. Catalysis Science and Technology. 2022 November; 12:7275-7280. doi: 10.1039/D2CY01805E.
Yang S, Li H, Yu X, An J, Szostak M. Suzuki-Miyaura Cross-Coupling of Aryl Fluorosulfonates Mediated by Air- and Moisture-stable [Pd(NHC)(μ-Cl)Cl](2) Precatalysts: Broad Platform for C-O Cross-Coupling of Stable Phenolic Electrophiles. J Org Chem. 2022 Nov 18;87(22):15250-15260. doi: 10.1021/acs.joc.2c01778. Epub 2022 Oct 28. PubMed PMID: 36305513.
Liu S, Liang J, Zhang P, Li Z, Jiao L, Jia W, Ma Y, Szostak M. Ruthenium-Catalyzed Divergent Deaminative and Denitrative C–N Cleavages: Facile Access to Quinoxalines. Organic Chemistry Frontiers. 2022 November; 10:22-29. doi: 10.1039/D2QO01572B.
Zhang J, Liu J, Wang X, Yang X, Ma Y, Fang R, Zhao Q, Szostak M. Ruthenium-Catalyzed C–F Bond Arylation of Polyfluoroarenes: Polyfluorinated Biaryls by Integrated C–F/C–H Functionalization. ACS Catalysis. 2022 November; 12(22):14337–14346. doi: 10.1021/acscatal.2c04401.
Zhou T, Gao P, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. Well-Defined, Air- and Moisture-Stable Palladium-Imidazo[1,5-a]pyridin-3-ylidene Complexes: A Versatile Catalyst Platform for Cross-Coupling Reactions by L-Shaped NHC Ligands. Catal Sci Technol. 2022 Nov 7;12(21):6581-6589. doi: 10.1039/d2cy01136k. Epub 2022 Sep 22. PubMed PMID: 38045636; PubMed Central PMCID: PMC10691866.
Rahman MM, Zhao Q, Meng G, Szostak R, Szostak M. [Ni(Np#)(η5-Cp)Cl]: Flexible, Sterically Bulky, Well-Defined, Highly Reactive Complex for Nickel-Catalyzed Cross-Coupling. Organometallics. 2022 Sep 26;41(18):2597-2604. doi: 10.1021/acs.organomet.2c00316. Epub 2022 Sep 2. PubMed PMID: 38031540; PubMed Central PMCID: PMC10686542.
Zhou T, Gao P, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. Well-Defined, Air- and Moisture-Stable Palladium–Imidazo[1,5-a]pyridin-3-ylidene Complexes: A Versatile Catalyst Platform for Cross-Coupling Reactions by L-Shaped NHC Ligands. Catalysis Science and Technology. 2022 September; 12:6581-6589. doi: 10.1039/D2CY01136K.
Rahman M, Zhao Q, Meng G, Szostak R, Szostak M. “[Ni(Np#)(h5-Cp)Cl]: Flexible, Sterically Bulky, Well-Defined, Highly Reactive Complex for Nickel-Catalyzed Cross-Coupling. Organometallics. 2022 September; 41. doi: doi.org/10.1021/acs.organomet.2c00316.
Lei P, Wang Y, Zhang C, Hu Y, Feng J, Ma Z, Liu X, Szostak R, Szostak M. Sonogashira Cross-Coupling of Aryl Ammonium Salts by Selective C-N Activation Catalyzed by Air- and Moisture-Stable, Highly Active [Pd(NHC)(3-CF(3)-An)Cl(2)] (An = Aniline) Precatalysts. Org Lett. 2022 Sep 2;24(34):6310-6315. doi: 10.1021/acs.orglett.2c02534. Epub 2022 Aug 24. PubMed PMID: 36001796.
Tomasini M, Zhang J, Zhao H, Besalú E, Falivene L, Caporaso L, Szostak M, Poater A. A predictive journey towards trans-thioamides/amides. Chem Commun (Camb). 2022 Sep 1;58(71):9950-9953. doi: 10.1039/d2cc04228b. PubMed PMID: 35983851.
Zhao Q, Li G, Nareddy P, Jordan F, Lalancette R, Szostak R, Szostak M. Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N-C(X) Resonance. Angew Chem Int Ed Engl. 2022 Aug 26;61(35):e202207346. doi: 10.1002/anie.202207346. Epub 2022 Jul 26. PubMed PMID: 35776856; PubMed Central PMCID: PMC9398953.
Rahman MM, Zhang J, Zhao Q, Feliciano J, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. Pd-PEPPSI N-Heterocyclic Carbene Complexes from Caffeine: Application in Suzuki, Heck, and Sonogashira Reactions. Organometallics. 2022 Aug 22;41(16):2281-2290. doi: 10.1021/acs.organomet.2c00262. Epub 2022 Aug 11. PubMed PMID: 38031591; PubMed Central PMCID: PMC10686539.
Rahman M, Zhang J, Zhao Q, Feliciano J, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. Pd−PEPPSI N-Heterocyclic Carbene Complexes from Caffeine: Application in Suzuki, Heck, and Sonogashira Reactions. Organometallics. 2022 August; 41(16):2281-2290. doi: doi.org/10.1021/acs.organomet.2c00262.
Zhang J, Zhao H, Li G, Zhu X, Shang L, He Y, Liu X, Ma Y, Szostak M. Transamidation of thioamides with nucleophilic amines: thioamide N-C(S) activation by ground-state-destabilization. Org Biomol Chem. 2022 Aug 3;20(30):5981-5988. doi: 10.1039/d2ob00412g. PubMed PMID: 35441645.
Zhang J, Rahman M, Zhao Q, Feliciano J, Bisz E, Dziuk B, Lalancette R, Szostak R, Szostak M. N-Heterocyclic Carbene Complexes of Nickel(II) from Caffeine and Theophylline: Sustainable Alternative to Imidazol-2-ylidenes. Organometallics. 2022 Jul 25;41(14):1806-1815. doi: 10.1021/acs.organomet.2c00019. Epub 2022 Apr 5. PubMed PMID: 36213557; PubMed Central PMCID: PMC9534456.
Zhang J, Li T, Li X, Zhang G, Fang S, Yan W, Li X, Yang X, Ma Y, Szostak M. An air-stable, well-defined palladium-BIAN-NHC chloro dimer: a fast-activating, highly efficient catalyst for cross-coupling. Chem Commun (Camb). 2022 Jun 30;58(53):7404-7407. doi: 10.1039/d2cc02253b. PubMed PMID: 35694980.
Zuo D, Wang Q, Liu L, Huang T, Szostak M, Chen T. Highly Chemoselective Transamidation of Unactivated Tertiary Amides by Electrophilic N-C(O) Activation by Amide-to-Acyl Iodide Re-routing. Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202202794. doi: 10.1002/anie.202202794. Epub 2022 Apr 11. PubMed PMID: 35355386.
Zhang J, Li T, Li X, Lv A, Li X, Wang Z, Wang R, Ma Y, Fang R, Szostak R, Szostak M. Thiazol-2-ylidenes as N-Heterocyclic carbene ligands with enhanced electrophilicity for transition metal catalysis. Commun Chem. 2022 May 6;5(1):60. doi: 10.1038/s42004-022-00675-7. PubMed PMID: 36697942; PubMed Central PMCID: PMC9814509.
Zhang J, Wang Y, Zhang Y, Liu T, Fang S, Wang R, Ma Y, Fang R, Szostak R, Szostak M. Application of Indazolin-3-ylidenes in Catalysis: Steric Tuning of Nonclassical Formally Normal N-Heterocyclic Carbenes with Dual Electronic Character for Catalysis. Organometallics. 2022 April; 41(9):1115-1124. doi: doi.org/10.1021/acs.organomet.2c00140.
Zhang Y, Szostak M. Synthesis of Natural Products by C-H Functionalization of Heterocycless. Chemistry. 2022 Apr 19;28(22):e202104278. doi: 10.1002/chem.202104278. Epub 2022 Feb 17. Review. PubMed PMID: 35089624; PubMed Central PMCID: PMC9035081.
Li G, Xing Y, Zhao H, Zhang J, Hong X, Szostak M. Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation. Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202200144. doi: 10.1002/anie.202200144. Epub 2022 Feb 23. PubMed PMID: 35122374; PubMed Central PMCID: PMC8983593.
Zhang J, Zhang P, Ma Y, Szostak M. Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides. Org Lett. 2022 Apr 1;24(12):2338-2343. doi: 10.1021/acs.orglett.2c00519. Epub 2022 Mar 17. PubMed PMID: 35297638.
What would you like to do?