The Bandar Group

Innovation in Strong Base Chemistry

Publications at Colorado State

(click on title to link to publication)

38) Direct Benzylic C–H Etherification Enabled by Base-Promoted Halogen Transfer. Bone, K. I.†; Puleo, T. R.†; Delost, M. D.; Shimizu, Y.; Bandar, J. S. Angew. Chem. Int. Ed. 2024, accepted. [Preprint posted to ChemRxiv] † Equal contribution.

37) Direct C–H Hydroxylation of N-Heteroarenes and Benzenes via Base-Catalyzed Halogen Transfer. Bone, K. I.; Puleo, T. R.; Bandar, J. S. J. Am. Chem. Soc. 2024, 146, 9755-9767.

36) A Strategy for the Controllable Generation of Organic Superbases from Benchtop-Stable Salts. Sujansky, S. J.†; Hoteling, G. A.†; Bandar, J. S. Chem. Sci. 2024, Advance Article. [Preprint posted to ChemRxiv. DOI: 10.26434/chemrxiv-2024-gt53w.] † Equal contribution.

35) Synthetic Advantages of Defluorinative C–F Bond Functionalization. Hooker, L. V.; Bandar, J. S. Angew. Chem. Int. Ed. 2023, e202308880.

34) C–H etherification via base-catalyzed X-transfer. Bone, K. I.; Bandar, J. S. Trends in Chemistry 2023. [Mechanism of the Month highlight article]

33) A Base-Catalyzed Approach for the anti-Markovnikov Hydration of Styrene Derivatives. Pajk, S. P.; Qi, Z.; Sujansky, S. J.; Bandar, J. S. Chem. Sci. 2022, 13, 11427-11432.

32) A Base-Promoted Reductive Coupling Platform for the Divergent Defluorofunctionalization of Trifluoromethylarenes. Wright, S. E.; Bandar, J. S. J. Am. Chem. Soc. 2022, 144, 13032-13038.

31) Mechanistic Studies Yield Improved Protocols for Base-Catalyzed anti-Markovnikov Alcohol Addition Reactions. Luo, C.; Alegre-Requena, J. V.; Sujansky, S. J.; Pajk, S. P.; Gallegos, L. C.; Paton, R. S.; Bandar, J. S. J. Am. Chem. Soc. 2022, 144, 9586-9596.

30) 2,3-Diiodobenzo[b]thiophene. Puleo, T. R.; Bandar, J. S. Encyclopedia for Reagents in Organic Synthesis 2022, DOI: 10.1002/047084289X.rn02468.

29) 2-Iodothiophene. Puleo, T. R.; Bandar, J. S. Encyclopedia for Reagents in Organic Synthesis 2022, DOI: 10.1002/047084289X.rn02467.

28) 2,5-Dibromothiophene. Puleo, T. R.; Bandar, J. S. Encyclopedia for Reagents in Organic Synthesis 2022, DOI: 10.1002/047084289X.rn02466.

27) Nucleophilic C–H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer. Puleo, T. R.; Klaus, D. R.; Bandar, J. S. J. Am. Chem. Soc. 2021, 143, 12480-12486.

26) Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles. Reidl, T. W.; Bandar, J. S. J. Am. Chem. Soc. 2021, 143, 11939-11945.

Organosilane arylation.png

25) Organic Superbases in Recent Synthetic Methodology Research. Puleo, T. R.; Sujansky, S. J.; Wright, S. E.; Bandar, J. S. Chem. Eur. J. 2021, 27, 4216-4229.

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24) Base-Catalyzed Aryl Halide Isomerization Enables the 4-Selective Substitution of 3-Bromopyridines. Puleo, T. R.; Bandar, J. S. Chem. Sci. 2020, 11, 10517-10522. [Preprint posted to ChemRxiv on March 25, 2020].

ArX TOC.png

23) Selective Defluoroallylation of Trifluoromethylarenes. Luo, C.; Bandar, J. S. J. Am. Chem. Soc. 2019, 141, 14120-14125.

22) Catalytic α-Selective Deuteration of Styrene Derivatives. Puleo, T. R.; Strong, A. J.; Bandar, J. S. J. Am. Chem. Soc. 2019, 141, 1467-1472.

21) Synthesis of β-Phenethyl Ethers via Base-Catalyzed Alcohol Addition Reactions to Aryl Alkenes. Luo, C.; Bandar, J. S. Synlett 2018, 29, 2218-2224 (Synpacts review article).

20) Superbase-Catalyzed anti-Markovnikov Alcohol Addition Reactions to Aryl Alkenes. Luo, C.; Bandar, J. S. J. Am. Chem. Soc. 2018, 140, 3547-3550.

Alcohol addition.png

Publications from MIT and Columbia

(click on title to link to publication)

19) Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines. Seibel, Z.M.; Bandar, J. S.; Lambert, T. H. Beilstein J. Org. Chem. 2021, 17, 2077-2084.

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18) Self-Assembly of Aminocyclopropenium Salts: En Route to Deltic Ionic Liquid Crystals. Litterscheidt, J.; Bandar, J. S.; Ebert, M.; Forschner, R.; Bader, K.; Lambert, T. H.; Frey, W.; Bühlmeyer, A.; Brändle, M.; Schulz, F.; Laschat, S. Angew. Chem. Int. Ed. 2020, 59, 10557-10565.

17) CuH‐Catalyzed Asymmetric Hydroamidation of Vinylarenes. Zhou, Y.; Engl, O. D.; Bandar, J. S.; Chant, E. D.; Buchwald, S. L. Angew. Chem. Int. Ed. 2018, 57, 6672-6675.

16) When size matters: exploring the potential of aminocyclopropenium cations as head groups in triphenylene-derived ionic liquid crystals in comparison with guanidinium and ammonium units. Litterscheidt, J.; Judge, P.; Bühlmeyer, A.; Badar, K.; Bandar, J. S.; Lambert, T. H.; Laschat, S. Liq. Cryst. 2018, 45, 1250-1258.

15) CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes. Zhou, Y.; Bandar, J. S.; Liu, R. Y.; Buchwald, S. L. J. Am. Chem. Soc. 2018, 140, 606-609.

14) Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. Zhou, Y.; Bandar, J. S.; Buchwald, S. L. J. Am. Chem. Soc. 2017, 139, 8126-8129.

13) Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles. Gribble, M. W. Jr.; Pirnot, M. T.; Bandar, J. S.; Liu, R. Y.; Buchwald, S. L. J. Am. Chem. Soc. 2017, 139, 2192-2195.

12) Clickable Poly(ionic liquids): A Materials Platform for Transfection. Freyer, J. L.; Brucks, S. D.; Gobieski, G. S.; Russell, S. T.; Yozwiak, C. E.; Sun, M.; Chen. Z.; Jiang, Y.; Bandar, J. S.; Stockwell, B. R.; Lambert, T. H.; Campos, L. M. Angew. Chem. Int. Ed. 2016, 55, 12382-12386.

11) Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids. Bandar, J. S.; Ascic, E.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 5821-5824.

10) Mechanistic Studies Lead to Dramatically Improved Reaction Conditions for the Cu-Catalyzed Asymmetric Hydroamination of Olefins. Bandar, J. S.; Pirnot, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 14812-14818.

9) Cyclopropenimine Superbases: Competitive Initiation Processes in Lactide Polymerization. Stukenbroeker, T. S.; Bandar, J. S.; Zhang, X.; Lambert, T. H.; Waymouth, R. M. ACS Macro Lett. 2015, 4, 853-856.

8) Phase-Transfer and Other Types of Catalysis with Cyclopropenium Ions. Bandar, J. S.; Tanaset, A.; Lambert, T. H. Chem. Eur. J. 2015, 21, 7365-7368.

7) The Evolution of Cyclopropenium Ions into Functional Polyelectrolytes. Jiang, Y.; Freyer, J. L.; Cotanda, P.; Brucks, S. D.; Killops, K. L.; Bandar, J. S.; Torsitano, C.; Balsara, N. P.; Lambert, T. H.; Campos, L. M. Nature Comm. 2015, Article number 5950.

6) Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Bronsted Base Catalysts. Bandar, J. S.; Barthelme, A. P.; Mazori, A. Y.; Lambert, T. H. Chem. Sci. 2015, 6, 1537-1547.

5) Transition State Analysis of Enantioselective Brønsted Base Catalysis by Chiral Cyclopropenimines. Bandar, J. S.; Sauer, G. S.; Wulff, W. D.; Lambert, T. H.; Vetticatt, M. J. J. Am. Chem. Soc. 2014, 136, 10700-10707.

4) Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of t-Butyl Glycinates with N-Boc-Imines. Bandar, J. S.; Lambert, T. H. J. Am. Chem. Soc. 2013, 135, 11799-11802.

3) Aminocyclopropenium Ions: Synthesis, Properties, and Applications. Bandar, J. S.; Lambert, T. H. Synthesis, 2013, 45, 2485-2498.

2) Enantioselective Brønsted Base Catalysis with Chiral Cyclopropenimines. Bandar, J. S.; Lambert, T. H. J. Am. Chem. Soc. 2012, 134, 5552-5555.

1) Demonstration of the Facile Reversibility of Fulvene Formation. Bandar, J. S.; Coscia, R. W.; Lambert, T. H. Tetrahedron, 2011, 67, 4364-4370.

Filed Patents from Columbia

2) Campos, L. M.; Lambert, T. H.; Dell, E. J.; Bandar, J. S. “Cyclopropenium Polymers and Methods for Making the Same.” World patent: WO2014022365 A1; 2014.

1) Lambert, T. H.; Bandar, J. S. “Cyclopropenimine Catalyst Compositions and Processes.” World patent: WO2013059118 A1; 2013.