Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
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 Jul 1;:e202207346. doi: 10.1002/anie.202207346. [Epub ahead of print] PubMed PMID: 35776856; NIHMSID:NIHMS1821112.
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.
Cervantes-Reyes A, Smith AC, Chinigo GM, Blakemore DC, Szostak M. Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls. Org Lett. 2022 Mar 4;24(8):1678-1683. doi: 10.1021/acs.orglett.2c00267. Epub 2022 Feb 24. PubMed PMID: 35200025; PubMed Central PMCID: PMC9069322.
Zhang J, Zhang P, Shao L, Wang R, Ma Y, Szostak M. Mechanochemical Solvent-Free Suzuki-Miyaura Cross-Coupling of Amides via Highly Chemoselective N-C Cleavage. Angew Chem Int Ed Engl. 2022 Feb 7;61(7):e202114146. doi: 10.1002/anie.202114146. Epub 2021 Dec 29. PubMed PMID: 34877756.
Li DH, Lan XB, Song AX, Rahman MM, Xu C, Huang FD, Szostak R, Szostak M, Liu FS. Buchwald-Hartwig Amination of Coordinating Heterocycles Enabled by Large-but-Flexible Pd-BIAN-NHC Catalysts. Chemistry. 2022 Jan 19;28(4):e202103341. doi: 10.1002/chem.202103341. Epub 2021 Dec 2. PubMed PMID: 34773313.
Liu C, Szostak M. Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles. Org Chem Front. 2022 Jan 7;9(1):216-222. doi: 10.1039/d1qo01539g. Epub 2021 Nov 19. PubMed PMID: 35495770; PubMed Central PMCID: PMC9049177.
Zhang W, Bie F, Ma J, Zhou F, Szostak M, Liu C. Palladium-Catalyzed Decarbonylative Borylation of Aryl Anhydrides. J Org Chem. 2021 Dec 3;86(23):17445-17452. doi: 10.1021/acs.joc.1c02134. Epub 2021 Nov 8. PubMed PMID: 34747599.
Liu C, Szostak M. Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles. Organic Chemistry Frontiers. 2021 November. doi: 10.1039/D1QO01539G.
Xia Q, Shi S, Gao P, Lalancette R, Szostak R, Szostak M. [(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions. J Org Chem. 2021 Nov 5;86(21):15648-15657. doi: 10.1021/acs.joc.1c02183. Epub 2021 Oct 7. PubMed PMID: 34619970; PubMed Central PMCID: PMC9097926.
Meng G, Zhang J, Szostak M. Acyclic Twisted Amides. Chem Rev. 2021 Oct 27;121(20):12746-12783. doi: 10.1021/acs.chemrev.1c00225. Epub 2021 Aug 18. Review. PubMed PMID: 34406005; PubMed Central PMCID: PMC9108997.
Lei P, Wang Y, Mu Y, Wang Y, Ma Z, Feng J, Liu X, Szostak M. Green-Solvent Selection for Acyl Buchwald–Hartwig Cross-Coupling of Amides (Transamidation). ACS Sustainable Chem. Eng.. 2021 October; 9(44):14937-14945. doi: 10.1021/acssuschemeng.1c05307.
Bie F, Liu X, Cao H, Shi Y, Zhou T, Szostak M, Liu C. Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters. Org Lett. 2021 Oct 15;23(20):8098-8103. doi: 10.1021/acs.orglett.1c03232. Epub 2021 Oct 5. PubMed PMID: 34609150.
Durand C, Szostak M. Recent Advances in the Synthesis of Piperazines: Focus on C–H Functionalization. Organics. 2021 October; 2(4):337-347. doi: 10.3390/org2040018.
Liu C, Szostak M. Forging C–S Bonds Through Decarbonylation. ChemCatChem. 2021 September; 13(23):4878-4881. doi: 10.1002/cctc.202101206.
Liu C, Szostak M. Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture. Org Chem Front. 2021 Sep 7;8(17):4805-4813. doi: 10.1039/d1qo00824b. Epub 2021 Jun 22. PubMed PMID: 34745635; PubMed Central PMCID: PMC8570612.
Bisz E, Koston M, Szostak M. N-Butylpyrrolidone (NBP) as a Non-Toxic Substitute for NMP in Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorides. Green Chemistry. 2021 August; 23(19):7515-7521. doi: 10.1039/D1GC02377B.
Zhao Q, Meng G, Li G, Flach C, Mendelsohn R, Lalancette R, Szostak R, Szostak M. IPr# - highly hindered, broadly applicable N-heterocyclic carbenes. Chem Sci. 2021 Aug 11;12(31):10583-10589. doi: 10.1039/d1sc02619d. eCollection 2021 Aug 11. PubMed PMID: 34447551; PubMed Central PMCID: PMC8356752.
Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters. J Org Chem. 2021 Aug 6;86(15):10829-10837. doi: 10.1021/acs.joc.1c01117. Epub 2021 Jul 9. PubMed PMID: 34240599.
Rahman MM, Pyle DJ, Bisz E, Dziuk B, Ejsmont K, Lalancette R, Wang Q, Chen H, Szostak R, Szostak M. Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions. J Org Chem. 2021 Aug 6;86(15):10455-10466. doi: 10.1021/acs.joc.1c01110. Epub 2021 Jul 17. PubMed PMID: 34275281.
Liu C, Szostak M. Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids. Org Lett. 2021 Jun 18;23(12):4726-4730. doi: 10.1021/acs.orglett.1c01445. Epub 2021 Jun 7. PubMed PMID: 34096312; PubMed Central PMCID: PMC9069321.
Rahman MM, Szostak M. Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation. Org Lett. 2021 Jun 18;23(12):4818-4822. doi: 10.1021/acs.orglett.1c01535. Epub 2021 Jun 7. PubMed PMID: 34096314.
Li H, Peng M, Lai Z, Ning L, Chen X, Zhang X, Wang P, Szostak R, Szostak M, An J. Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI2 and D2O. Chem Commun (Camb). 2021 May 25;57(42):5195-5198. doi: 10.1039/d1cc01381e. Epub 2021 Apr 28. PubMed PMID: 33908475.
Yang S, Zhou T, Poater A, Cavallo L, Nolan SP, Szostak M. Suzuki-Miyaura Cross-Coupling of Esters by Selective O-C(O) Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Catalyst Evaluation and Mechanism. Catal Sci Technol. 2021 May 7;11(9):3189-3197. doi: 10.1039/d1cy00312g. Epub 2021 Mar 25. PubMed PMID: 34211698; PubMed Central PMCID: PMC8240519.
Liu C, Ji CL, Zhou T, Hong X, Szostak M. Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling. Angew Chem Int Ed Engl. 2021 May 3;60(19):10690-10699. doi: 10.1002/anie.202100949. Epub 2021 Apr 6. PubMed PMID: 33596335; PubMed Central PMCID: PMC8085135.
Mughal H, Szostak M. Recent advances in the synthesis and reactivity of azetidines: strain-driven character of the four-membered heterocycle. Org Biomol Chem. 2021 Apr 26;19(15):3274-3286. doi: 10.1039/d1ob00061f. Review. PubMed PMID: 33899862.
Shi Y, Liu X, Cao H, Bie F, Han Y, Yan P, Szostak R, Szostak M, Liu C. Conversion of esters to thioesters under mild conditions. Org Biomol Chem. 2021 Apr 7;19(13):2991-2996. doi: 10.1039/d1ob00187f. Epub 2021 Mar 18. PubMed PMID: 33734267.
Urbina K, Tresp D, Sipps K, Szostak M. Recent Advances in Metal-Catalyzed Functionalization of Indoles. Advanced Synthesis Catalysis. 2021 April; 363(11):2723-2739. doi: 10.1002/adsc.202100116.
Chen C, Liu FS, Szostak M. BIAN-NHC Ligands in Transition-Metal-Catalysis: A Perfect Union of Sterically Encumbered, Electronically Tunable N-Heterocyclic Carbenes?. Chemistry. 2021 Mar 8;27(14):4478-4499. doi: 10.1002/chem.202003923. Epub 2021 Jan 18. Review. PubMed PMID: 32989914; PubMed Central PMCID: PMC7940599.
Nan J, Zhang J, Hu Y, Wang C, Wang T, Wang W, Ma Y, Szostak M. CuII-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages. Org Lett. 2021 Mar 5;23(5):1928-1933. doi: 10.1021/acs.orglett.1c00371. Epub 2021 Feb 11. PubMed PMID: 33570962.
Szostak M, Rahman M, inventors. Rutgers University, assignee. Sterically Hindered N-Aliphatic N-Heterocylic Carbene Catalysts and Methods Using Same. United States 63/155,492. 2021 March.
Szostak M, Zhao Q, inventors. Rutgers University, assignee. Unsymmetrical N-Heterocyclic Carbene Catalysis and Methods Using Same. United States patent application 63/154,948. 2021 March.
Ning L, Li H, Lai Z, Szostak M, Chen X, Dong Y, Jin S, An J. Synthesis of α-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D2O as a Deuterium Source. J Org Chem. 2021 Feb 5;86(3):2907-2916. doi: 10.1021/acs.joc.0c02829. Epub 2021 Jan 25. PubMed PMID: 33486945.
Cao H, Liu X, Bie F, Shi Y, Han Y, Yan P, Szostak M, Liu C. General and practical intramolecular decarbonylative coupling of thioesters via palladium catalysis. Org. Chem. Front.. 2021 February. doi: 10.1039/D0QO01576H.
Buchspies J, Rahman MM, Szostak M. Transamidation of Amides and Amidation of Esters by Selective N-C(O)/O-C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)-NHC Complexes. Molecules. 2021 Jan 2;26(1). doi: 10.3390/molecules26010188. PubMed PMID: 33401664; PubMed Central PMCID: PMC7795584.
Lei P, Mu Y, Wang Y, Wang Y, Ma Z, Feng J, Liu X, Szostak M. Green Solvent Selection for Suzuki–Miyaura Coupling of Amides. ACS Sustainable Chem. Eng.. 2020 December; 9(1):552-559. doi: 10.1021/acssuschemeng.0c08044.
Zhang J, Liu Z, Yin Z, Yang X, Ma Y, Szostak R, Szostak M. Preference of cis-Thioamide Structure in N-Thioacyl-N-methylanilines. Org Lett. 2020 Dec 18;22(24):9500-9505. doi: 10.1021/acs.orglett.0c03512. Epub 2020 Nov 30. PubMed PMID: 33252240.
Ielo L, Pace V, Holzer W, Rahman MM, Meng G, Szostak R, Szostak M. Electrophilicity Scale of Activated Amides: 17 O NMR and 15 N NMR Chemical Shifts of Acyclic Twisted Amides in N-C(O) Cross-Coupling. Chemistry. 2020 Dec 9;26(69):16246-16250. doi: 10.1002/chem.202003213. Epub 2020 Nov 11. PubMed PMID: 32668046.
Bie F, Liu X, Shi Y, Cao H, Han Y, Szostak M, Liu C. Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides. J Org Chem. 2020 Dec 4;85(23):15676-15685. doi: 10.1021/acs.joc.0c02157. Epub 2020 Oct 30. PubMed PMID: 33124423.
Lei P, Li G, Ling Y, An J, Nolan SP, Szostak M. Protocol for Palladium/N-Heterocyclic Carbene-Catalyzed Suzuki–Miyaura Cross-Coupling of Amides by N–C(O) Activation. Synthesis. 2020 November; 53(04):682-687. doi: 10.1055/s-0040-1705956.
Chen P, Nan J, Hu Y, Kang Y, Wang B, Ma Y, Szostak M. Metal-free tandem carbene N-H insertions and C-C bond cleavages. Chem Sci. 2020 Nov 10;12(2):803-811. doi: 10.1039/d0sc05763k. PubMed PMID: 34163814; PubMed Central PMCID: PMC8178978.
Luo S, Weng C, Ding Y, Ling C, Szostak M, Ma X, An J. Reductive Deuteration of Aromatic Esters for the Synthesis of α,α-Dideuterio Benzyl Alcohols Using D2O as Deuterium Source. Synthesis. 2020 October; 32(1):51-56. doi: 10.1055/s-0040-1705944.
Piontek A, Ochędzan‐Siodłak W, Bisz E, Szostak M. Cobalt−NHC Catalyzed C(sp2)−C(sp3) and C(sp2)−C(sp2) Kumada Cross‐Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents. ChemCatChem. 2020 October; 13(1):202-206. doi: 10.1002/cctc.202001347.
Li G, Ma S, Szostal M. Amide Bond Activation: The Power of Resonance. Trends in Chemistry. 2020 September; 2(10):914-928. doi: 10.1016/j.trechm.2020.08.001.
Zhou T, Szostak M. Palladium-Catalyzed Cross-Couplings by C-O Bond Activation. Catal Sci Technol. 2020 Sep 7;10(17):5702-5739. doi: 10.1039/d0cy01159b. Epub 2020 Jul 30. PubMed PMID: 33796263; PubMed Central PMCID: PMC8009314.
Zhang J, Liu Y, Jia Q, Wang Y, Ma Y, Szostak M. Ruthenium(II)-Catalyzed C-H Arylation of N,N-Dialkyl Thiobenzamides with Boronic Acids by Sulfur Coordination in 2-MeTHF. Org Lett. 2020 Sep 4;22(17):6884-6890. doi: 10.1021/acs.orglett.0c02410. Epub 2020 Aug 18. PubMed PMID: 32809838.
Zhou T, Xie PP, Ji CL, Hong X, Szostak M. Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides. Org Lett. 2020 Aug 21;22(16):6434-6440. doi: 10.1021/acs.orglett.0c02250. Epub 2020 Aug 10. PubMed PMID: 32806154; PubMed Central PMCID: PMC7456303.
Zhou T, Ma S, Nahra F, Obled AMC, Poater A, Cavallo L, Cazin CSJ, Nolan SP, Szostak M. [Pd(NHC)(μ-Cl)Cl]2: Versatile and Highly Reactive Complexes for Cross-Coupling Reactions that Avoid Formation of Inactive Pd(I) Off-Cycle Products. iScience. 2020 Aug 21;23(8):101377. doi: 10.1016/j.isci.2020.101377. Epub 2020 Jul 16. PubMed PMID: 32759055; PubMed Central PMCID: PMC7404551.
Gao P, Szostak M. Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation. Org Lett. 2020 Aug 7;22(15):6010-6015. doi: 10.1021/acs.orglett.0c02105. Epub 2020 Jul 9. PubMed PMID: 32645265.
Wang X, Zhang J, He Y, Chen D, Wang C, Yang F, Wang W, Ma Y, Szostak M. Ruthenium(II)-Catalyzed Ortho-C-H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water. Org Lett. 2020 Jul 2;22(13):5187-5192. doi: 10.1021/acs.orglett.0c01811. Epub 2020 Jun 19. PubMed PMID: 32558578.
What would you like to do?