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1. A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones

Chem. Sci. 202213, 1095-1100. DOI: 10.1039/D1SC06968C

Luu, Q. H.; Li, J.*

Advances in site-selective functionalization reactions have enabled C to O 2022single atom changes on the periphery of a complex molecule, but reaction manifolds that enable such changes on the core framework of the molecule remain sparse. Here, we disclose a strategy for carbon-to-oxygen substitution in cyclic diarylmethanes and diarylketones to yield cyclic diarylethers. Oxygen atom insertion is accomplished by methylene and Baeyer-Villiger oxidations. To remove the carbon atom in this C-to-O “atom swap” process, we developed a nickel-catalyzed decarbonylation of lactones to yield the corresponding cyclic diaryl ethers. This reaction was enabled by mechanistic studies with stoichiometric nickel(II) complexes that led to the optimization of a ligand capable of promoting a challenging C(sp2)-O reductive elimination. The nickel-catalyzed decarbonylation was applied to 6-8 membered lactones (16 examples, 32-99%). Finally, a C-to-O atom-swapping reaction sequence was accomplished on a natural product and a pharmaceutical.


Before ISU


1. Site-Selective Acylation of Natural Products with BINOL-Derived Phosphoric Acids

ACS Catal. 2019, 9, 9794-9799. DOI: 10.1021/acscatal.9b03535

Li, J.*; Grosslight, S.*; Miller, S. J.; Sigman, M. S.; Toste, F. D.

*equal contribution


2. Disparate catalytic scaffolds for atroposelective cyclodehydration

J. Am. Chem. Soc. 2019, 141, 6698-6705. DOI: 10.1021/jacs.9b01911

Kwon, Y.; Li, J.; Reid, J. P.; Crawford, J. M.; Jacob, R.; Sigman, M. S.; Toste, F. D.; Miller, S. J.


3. Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of Csp3 boronic acids

Nat. Commun. 2019, 10, 1263. DOI: 10.1038/s41467-019-09249-z

Lehmann, J. W.*; Crouch, I. T.*; Blair, D. J.; Trobe, M.; Wang, P.; Li, J.; Burke, M. D.

*equal contribution


4. From synthesis to function via iterative assembly of MIDA boronate building blocks

Acc. Chem. Res. 2015, 48, 2297-2307. DOI: 10.1021/acs.accounts.5b00128

Li, J.; Grillo, A. S.; Burke, M. D.


5. Synthesis of many different types of organic small molecules using one automated process

Science 2015, 347, 1221-1226. DOI: 10.1126/science.aaa5414

Li, J.*; Ballmer, S. G.*; Gillis, E. P.; Fujii, S.; Schmidt, M. J.; Palazzolo, A. M. E.; Lehmann, J. W.; Morehouse, G. F. and Burke, M. D.

*equal contribution

  • Highlighted in Science, “The Synthesis Machine”
  • Highlighted in Nature, “Complex Molecules Made to Order in Synthesis Machine”
  • Also highlighted in C&EN News, Nature World News, HHMI News, Illinois News, Science Daily, eScience News, Phys Org, Scientific American, medGadget, STGIST, Popular Mechanics, HNGN, Huffington Post, Forbes, News Everyday, Design & Trend, ZME Science, Silicon Angle, Yibada,, Make Magazine, 3D Print, GizMag, Ecumenical News, and International Business Times.


6. Pinene-derived iminidodiacetic acid (PIDA): A powerful ligand for stereoselective synthesis and iterative cross-coupling of Csp3 boronate building blocks

J. Am. Chem. Soc. 2011, 133, 13774-13777. DOI: 10.1021/ja205912y

Li, J. and Burke, M. D.

    • Highlighted in Chemical and Engineering News 2011, 89(35), 5
    • Highlighted in Synfacts 2011, 11, 1229.


7. Rapid synthesis, screening and identification of Xanthone- and Xanthene-based fluorophores using click chemistry

Org. Lett. 2009, 11, 3008-3011. DOI: 10.1021/ol9010344

Li, J.; Hu, M.; Yao, S. Q.


8. ‘Singapore Green’ – A New Fluorescent Dye for Microarray and Bioimaging Applications

Org. Lett. 2009, 11, 405-408. DOI: 10.1021/ol802700w

Li, J. and Yao, S. Q.


9. In Situ ‘Click’ Assembly of Small Molecule Matrix Metalloprotease Inhibitors Containing Zinc-Chelating Groups

Org. Lett. 2008, 10, 5529-5531. DOI: 10.1021/ol802286g

Hu, M.; Li, J.; Yao, S. Q


10. Activity-Based Profiling: New Developments and Directions in Functional Proteomics

ChemBioChem 2008, 9, 667-675.  DOI: 10.1002/cbic.200700755

Uttamchandani, M; Li. J.; Sun, H.; Yao, S.Q.


11. Methods of Using Click Chemistry in the Discovery of Enzyme Inhibitors

Nature Protocols 2007, 2, 2655-2664. DOI: 10.1038/nprot.2007.323

Srinivasan, R.; Li, J.; Ng, S.L.; Kalesh, K.A.; Yao, S.Q.


12. Inhibitor Fingerprinting of Metalloproteases Using Microplate and Microarray Platforms – An Enabling Technology in Catalomics.

Nature Protocols 2007, 2, 2126-2138. DOI: 10.1038/nprot.2007.305

Lee, W.L.; Li, J.; Uttamchandani, M.; Sun, H.; Yao, S.Q.


13. Inhibitor Fingerprinting of Matrix Metalloproteases Using a Combinatorial Peptide Hydroxamate Library.

J. Am. Chem. Soc. 2007, 129, 13110-13117. DOI: 10.1021/ja070870h

Uttamchandani, M.; Wang, J.; Li, J.; Hu, M.; Sun, H.; Chen, K. Y.-T.; Liu, K.; Yao, S.Q.


14. ‘Click’ Synthesis of Small Molecule Probes for Activity-Based Fingerprinting of Matrix Metalloproteases

Chem. Commun. 2006, 3783-3785. DOI: 10.1039/B609446E

Wang, J.; Uttamchandani, M.; Li, J.; Hu, M.; Yao, S.Q.


15. Rapid Assembly of Matrix Metalloproteases (MMP) Inhibitors Using Click Chemistry

Org. Lett. 2006, 8, 3821-3824. DOI: 10.1021/ol061431a

Wang, J.; Uttamchandani, M.; Li, J.; Hu, M.; Yao, S.Q.



"Automated Synthesis of Small Molecules Using Chiral, Non-Racemic Boronates" M.D. Burke, J. Li, Gillis, E. P. WO/2012/149182