Publications

Journal Articles
41.

MacLeod, B. P.; Parlane, F. G. L.; Morrissey, T. D.; Häse, F.; Roch, L.; Dettelbach, K. E.; Moreira, R.; Yunker, L. P. E.; Rooney, M. B.; Deeth, J. R.; Lai, V.; Ng, G. J.; Situ, H.; Zhang, R. H.; Aspuru-Guzik, A.; Hein, J. E.; Berlinguette, C. P. “Self-driving Laboratory for Accelerated Discovery of Thin-Film Materials.” 2019.

(DOI: arXiv:1906.05398)
39.

Christensen, M.; Adedeji, F.; Grosser, S.; Zawatzky, K.; Ji, Y.; Liu, J.; Jurica, J. A.; Naber, J. R.; Hein, J. E. “Development of an automated kinetic profiling system with online HPLC for reaction optimization.” React. Chem. & Eng. 2019.

(DOI: 10.1039/C9RE00086K)
37.

Epifanov, M.; Foth, P. J.; Gu ,F.; Barrillon, C.; Kanani, S. S.; Higman, C. S.; Hein, J. E.; Sammis, G. M. “One-Pot 1,1-Dihydrofluoroalkylation of Amines Using Sulfuryl Fluoride.” J. Am. Chem. Soc. 2018, 140(48), p. 16464-16468.

(DOI: 10.1021/jacs.8b11309)
35.

Malig, T. C.; Yu, D. N.; Hein, J. E.* “A Revised Mechanism for the Kinugasa Reaction.” J. Am. Chem. Soc. 2018, 140(29), p. 9167–9173.

(DOI: 10.1021/jacs.8b04635)
34.

Roch, L. M.; Häse, F.; Kreisbeck, C.; Tamayo-Mendoza, T.; Yunker, L. P. E.; Hein, J. E.; Aspuru-Guzik, A.*: “ChemOS: Orchestrating autonomous experimentation.” Sci. Robot., 2018, 3(19).

(DOI: 10.1126/scirobotics.aat5559)
33.

Burford, R. J.; Castro, L.; Maron, L.; Hein, J. E.*; Fryzuk, M. D.*: “Dinitrogen functionalization at a ditantalum center. Balancing N-2 displacement and N-2 functionalization in the reaction of coordinated N-2 and CS2.” Dalton Trans., 2018, 47(24), p. 7983-7991.

(DOI: 10.1039/C8DT01615A)
32.

Das, U. K.; Higman, C. S.; Gabidullin, B.; Hein, J. E.*; Baker, R. T.*: “Efficient and Selective Iron-Complex-Catalyzed Hydroboration of Aldehydes.” ACS Catal., 2018, 8(2), p. 1076–1081.

(DOI: 10.1021/acscatal.7b03785)
31.

Phung, C.; Tantillo, D. J.; Hein, J. E.; Pinhas, A. R.*: “The Mechanism of the Reaction Between an Aziridine and Carbon Dioxide with No Added Catalyst.” J. Phys. Org. Chem., 2018, 31(1).

(DOI: 10.1002/poc.3735)
30.

Wilkerson-Hill, S. M.; Yu, D.; Painter, P. P.; Fisher, E. L.; Tantillo, D. J.*; Sarpong, R.*; Hein, J. E.*: “Mechanism of a No-Metal-Added Heterocycloisomerization of Alkynylcyclopropylhydrazones: Synthesis of Cycloheptane-Fused Aminopyrroles Facilitated by Copper Salts at Trace Loadings.” J. Am. Chem. Soc., 2017, 139(30), p. 10569 – 10577.

(DOI: 10.1021/jacs.7b06007)
29.

Higman, C. S.; Situ, H.; Blacklin, P.; Hein, J. E.*: “Hands-on Data Analysis: Using 3D Printing to Visualize Reaction Progress Surfaces.” J. Chem. Ed., 2017, 94(9), p. 1367 – 1371. DOI: 10.1021/acs.jchemed.7b00314.

(DOI: 10.1021/acs.jchemed.7b00314)
28.

Torabifard, H.; Reed, L.; Berry, M. T.; Hein, J. E.; Menke, E.; Cisneros, G. A.*: “Computational and Experimental Characterization of a Pyrrolidinium-Based Ionic Liquid for Electrolyte Applications.” J. Chem. Phys., 2017, 147(16), DOI: 10.1063/1.5004680.

(DOI: 10.1063/1.5004680)
27.

Soley, J.; Chiu, E.; Chung, R.; Green, J.; Hein, J. E.; Taylor, S. D.*: “Synthesis of β-Ketosulfonamides Derived from Amino Acids and Their Conversion to β-Keto-α,α-Difluorosulfonamides via Electrophilic Fluorination.” J. Org. Chem., 2017, 82(20), p. 11157–11165. DOI: 10.1021/acs.joc.7b02179.

(DOI: 10.1021/acs.joc.7b02179)
26.

Diemoz, K. M.; Hein, J. E.; Wilson, S. O.; Fettinger, J. C.; Franz, A. K*.: “Reaction Progress Kinetics Analysis of 1,3-Disiloxanediols as Hydrogen-Bonding Catalysts.” J. Org. Chem., 2017, 82(13), p. 6738 – 6747.

(DOI: 10.1021/acs.joc.7b00875)
25.

Lamb, K. N.; Squitieri, R. A.; Chintala, S. R.; Kwong, A. J.; Balmond, E. I.; Soldi, C.; Dmytrenko, O.; Reis, M. C.; Chung, R.; Addison, J. B.; Fettinger, J.C.; Hein, J. E.; Tantillo, D. J.; Fox, J. M.; Shaw, J. T.*: “Synthesis of Benzodihydrofurans by Asymmetric C-H Insertion Reactions of Donor/Donor Rhodium Carbenes.” Chem. Eur. J., 2017, 23(49), p. 11843 – 11855.

(DOI: 10.1002/chem.201701630)
24.

Chung, R.; Vo, A.; Hein, J. E.* “Copper-Catalyzed Hydrogen/Iodine Exchange in Terminal and 1-Iodoalkynes.” ACS Catal., 2017, 7(4), p. 2505–2510.

(DOI: 10.1021/acscatal.6b03515)
23.

Weatherly, C.; Alderson, J. M.; Berry, J. F.*; Hein, J. E.*; Schomaker, J. M.*: “Catalyst-Controlled Nitrene Transfer by Tuning Metal:Ligand Ratios: Insight into the Mechanisms of Chemoselectivity.” Organometallics, 2017, 36 (8), p. 1649–1661.

(DOI: 10.1021/acs.organomet.7b00190)
22.

Malig, T. C.; Koenig, J. D. B.; Situ, H.; Chehal, N. K.; Hultin, P. G.; Hein, J. E.*: “Real-Time HPLC-MS Reaction Progress Monitoring Using an Automated Analytical Platform.” React. Chem. Eng., 2017, 2(3), p. 309-314.

(DOI: 10.1039/C7RE00026J)
20.

Rougeot, C.; Situ, H.; Cao, B. H.; Vlachos, V.; Hein, J. E.*: “Automated Reaction Progress Monitoring of Heterogeneous Reactions: Crystallization-Induced Stereoselectivity in Amine-Catalyzed Aldol Reactions.” React. Chem. Eng., 2017, 2(2), p. 226 – 231.

(DOI: 10.1039/C6RE00211K)
19.

Otero-de-la-Roza, A.; Hein, J. E.*; Johnson, E. R.*: “Reevaluating the Stability and Prevalence of Conglomerates: Implications for Preferential Crystallization.” Cryst. Growth Des.2016, 16(10), p. 6055 – 6059.

(DOI: 10.1021/acs.cgd.6b01088)
18.

Squitieri, R. A.; Shearn-Nance, G. P.; Hein, J. E.; Shaw, J. T.*: “Synthesis of Esters by in Situ Formation and Trapping of Diazoalkanes.” J. Org. Chem., 2016, 81(13), p. 5278 – 5284.

(DOI: 10.1021/acs.joc.6b00408)
17.

Able Jr., G. R.; Calabrese, Z. A.; Ayco, J.; Hein, J. E.*; Ye, T.*: “Measuring and Suppressing the Oxidative Damage to DNA During Cu(I)-Catalyzed Azide-Alkyne Cycloaddition.” Bioconjug. Chem., 2016, 27(3), p. 698 – 704.

(DOI: 10.1021/acs.bioconjchem.5b00665)
16.

Rougeot, C.; Hein, J. E.*: “Application of Continuous Preferential Crystallization to Efficiently Access Enantiopure Chemicals.” Org. Proc. Res. Dev., 2015, 19(12), p. 1809 – 1819.

(DOI: 10.1021/acs.oprd.5b00141)
15.

Rodarte, A.L.; Cisnero, F. Hein, J. E.*; Ghosh, S.*; Hirst, L.*: “Quantum Dot/Liquid Crystal Nanocomposites in Photonic Devices.” Photonics, 2015, 2(3), p. 855 – 864.

(DOI: 10.3390/photonics2030855)
14.

Chung, R.; Yu, D.; Thai, V. T.; Jones, A. F.; Veits, G. K.; Read de Alaniz, J.; Hein, J. E.*: “Tandem Reaction Progress Analysis as a Means of Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement.” ACS Catal., 2015, 5(8), p. 4579 – 4585.

(DOI: 10.1021/acscatal.5b01087)
13.

Veits, G, K; Wenz, D. R.; Palmer, L. I.; Hein, J. E.; Read de Alaniz, J.*: “Cascade Rearrangement of Furylcarbinols with Hydroxylamines: Practical Access to Densely Functionalized Cyclopentane Derivatives.” Org. Biomol. Chem., 2015, 13(31), p. 8465 – 8469.

(DOI: 10.1039/C5OB00944H)
12.

Price, I.K.; Rougeot, C.; Hein, J. E.*: “Crystal Structure of racemic 5,7-diphenyl-4,7-dihydrotetrazolo-[1,5a] pyrimidine.” Acta Cryst., 2015, 71(3), p. 192.

(DOI: 10.1107/S2056989015002984)
11.

Price, I.K.; Rougeot, C.; Hein, J. E.*: “Crystal Structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo-[1,5a] pyrimidine.” Acta Cryst., 2015, 71(4), p. 220-221.

(DOI: 10.1107/S2056989015002996)
10.

Rodarte, A.L.; Cao, B. H.; Panesar, H.; Pandolfi, R.J.; Quint, M.; Edwards, L.; Ghosh, S.*; Hein, J. E.; Hirst, L.S.: “Self-Assembled Nanoparticle Micro-Shells Templated by Liquid Crystal Sorting.” Soft Matter, 2015, 11(9), p. 1701 – 1707.

(DOI: 10.1039/C4SM02326A)
9.

Berry, M. T.; Casterjon, D.; Hein, J. E*.: “Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts.” Org. Lett., 2014, 16(14), p. 3676 – 3679.

(DOI: 10.1021/ol501458p)
8.

Abel, G. R.; Cao, B. H.; Hein, J. E.; Ye, T.* “Covalent, Sequence-Specific Attachment of Long DNA Molecules to a Surface Using DNA-Templated Click Chemistry.” Chem. Commun., 2014, 50(60), p. 8131 – 8133.

(DOI: 10.1039/C4CC02900C)
7.

Otero-de-la-Roza, A.; Cao, B. H.; Price, I. K.; Hein, J. E.; Johnson, E. R. “Predicting the Relative Solubilities of Racemic and Enantiopure Crystals by Density-Functional Theory.” Angew. Chem. Int. Ed., 2014, 53(30), p. 7879 – 7882.

(DOI: 10.1002/anie.201403541)
6.

Rodarte, A. L.; Nuno, Z. S.; Cao, B. H.; Pandolfi, R. J.; Quint, M. T.; Ghosh, S.*; Hein, J. E.*; Hirst, L. S.* “Tuning Quantum-Dot Organization in Liquid Crystals for Robust Photonic Applications.” Chemphyschem, 2014, 15(7), p. 1413 – 1421.

(DOI: 10.1002/cphc.201301007)
5.

Yu, D.; Thai, V. T.; Palmer, L. I.; Veits, G. K.; Cook, J. E.; Read de Alaniz, J.; Hein, J. E.* “Importance of Off-Cycle Species in the Acid-Catalyzed Aza-Piancatelli Rearrangement.” J. Org. Chem., 2013, 78(24), p.  12784 – 12789.

(DOI: 10.1021/jo402155b)
4.

Hein, J. E.*; Cao, B. H.; van der Meijden, M.; Leeman, M.; Kellogg, R. M.* “Resolution of Omeprazole Using Coupled Preferential Crystallization: Efficient Separation of a Nonracemizable Conglomerate Salt under Near-Equilibrium Conditions.” Org. Process Res. Dev., 2013, 17(6), p. 946 – 950.

(DOI: 10.1021/op400081c)
3.

Burton, A. S.; Elsila, J. E.; Hein, J. E.; Galvin, D. P.; Dworkin, J. P.* “Extraterrestrial amino acids identified in metal-rich CH and CB Carbonaceous Chondrites from Antarctica.” Meteorit. Planet. Sci., 2013, 48(3), p. 390 – 402.

(DOI: 10.1111/maps.12063)
2.

Hein, J. E.; Gherase, D.; Blackmond, D. G. “Chemical and Physical Models for the Emergence of Biological Homochirality.” Top. Curr. Chem., 2013, 333, p. 83 – 108.

(DOI: 10.1007/128_2012_397)
1.

Hein, J. E.; Cao, B. H.; Viedma, C.; Kellogg, R. M.; Blackmond, D. G.* “Pasteur’s Tweezers Revisited: On the Mechanism of Attrition-Enhanced Deracemization and Resolution of Chiral Conglomerate Solids.” J. Am. Chem. Soc., 2012, 134(30), p. 12629 – 12636.

(DOI: 10.1021/ja303566g)
Prior Publications
16.

Worrell, B. T.; Hein, J. E.; Fokin, V. V. “Halogen Exchange (Halex) Reaction of 5-Iodo-1,2,3-triazoles: Synthesis and Applications of 5-Fluorotriazoles.” Angew. Chem. Int. Ed., 2012, 51(47), p. 11791 – 11794.

15.

Hein, J. E.; Blackmond, D. G. “On the Origin of Single Chirality of Amino Acids and Sugars in Biogenesis.” Acc. Chem. Res., 2012, 45(12), p. 2045 – 2054.

14.

Hein, J. E.; Bures, J.; Lam Y-H; Hughes, M.; Houk, K. N.; Armstrong, A.; Blackmond, D. G. “Enamine Carboxylates as Stereodetermining Intermediates in Prolinate Catalysis.” Org. Lett., 2011, 13(20), p. 5644 – 5647.

13.

Millward, S. W.; Henning, R. K.; Kwong, G. A.; Pitram, S.; Agnew, H. D.; Deyle, K. M.; Nag, A.; Hein, J. E.; Lee, S. S.; Lim, J.; Pfeilsticker, J. A.; Sharpless, K. B.; Heath, J. R. “Iterative in Situ Click Chemistry Assembles a Branched Capture Agent and Allosteric Inhibitor for Akt1.” J. Am. Chem. Soc., 2011, 133(45), p. 18280 – 18288.

12.

Hein, J. E.; Tse, E.; Blackmond, D. G. “A Route to Enantiomerically Pure RNA Precursors from Nearly Racemic Starting Materials.” Nature. Chem., 2011, 3(9) , p. 704 – 706.

11.

Hein, J. E.; Armstrong, A.; Blackmond, D. G. “Kinetic Profiling of Prolinate-Catalyzed α-Amination of Aldehydes.” Org. Lett., 2011, 13(16), p. 4300 – 4303.

10.

Hein, J. E.; Krasnova, L. B.; Iwasaki, M.; Fokin, V. V. “Cu-catalyzed azide-alkyne cycloaddition: Preparation of Tris((1-benzyl-1H-1,2,3-triazolyl)methyl)amine.” Org. Synth., 2011, 88, p. 238 – 246.

9.

Krasnova, L. B.; Hein, J. E.; Fokin, V. V. “Synthesis of 7-Aza-5-deazapurine Analogs via Copper (I)-catalyzed Hydroamination of Alkynes and 1-Iodoalkynes.” J. Org. Chem., 2010, 75(24), p. 8662 – 8665.

8.

Hein, J. E.; Fokin, V. V. “Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Beyond: New Reactivity or Copper(I) Acetylides.” Chem Soc. Rev., 2010, 39(4), p. 1302 – 1315.

7.

Hein, J. E.; Tripp. J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. “Copper(I)-Catalyzed Cycloaddition of Organic Azides and 1-Iodoalkynes.” Angew. Chem. Int. Ed., 2009, 48(43), p. 8018 – 8021.

6.

Agnew, H. D.; Rohde, R. D.; Millward, S. W.; Nag, A.; Yeo W.-S.; Hein, J. E.; Pitram, S. M.; Tariq, A. A.; Burns; Krom, R. J.; Fokin, V. V.; Sharpless, K. B.; Heath, J. R., “Iterative In Situ Click Chemistry Creates Antibody-like Protein Capture Agents.” Angew. Chem. Int. Ed., 2009, 48(27), p. 4944 – 4948.

5.

Kwok, S. W.; Hein, J. E.; Fokin, V. V.; Sharpless, K. B. “Regioselective Synthesis of Either 1H– or 2H-1,2,3-Triazoles via Michael Addition to α,β-Unsaturated Ketones.” Heterocycles, 2008, 76(2), p. 1141 – 1154.

4.

Hein, J. E.; Geary, L. M.; Jaworski, A. A.; Hultin, P. G. “Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α–Amino Acids.” J. Org. Chem., 2005, 70(24), p. 9940 – 9946.

3.

Hein, J. E.; Hultin, P. G. “Recyclable Supports for Stereoselective 1,3-Dipolar Cycloadditions: Application of a Fluorous Oxazolidinone Chiral Auxiliary.” Tetrahedron Asymm., 2005, 16(13), p. 2341 – 2347.

2.

Hein, J. E.; Zimmerman, J.; Sibi, M. P.; Hultin, P. G. “Stereoselective Conjugate Radical Additions: Application of a Fluorous Oxazolidinone Chiral Auxiliary for Efficient Tin Removal.” Org. Lett., 2005, 7(13), p. 2755 – 2758.

1.

Hein, J. E.; Hultin, P. G. “Asymmetric Aldol Reactions Using a Fluorous Oxazolidinone Chiral Auxiliary.” Synlett, 2003, 5, p. 635 – 638.