Guangbin Dong

Weldon G. Brown Professor
Research and Scholarly Interests: Organic Chemistry, Catalysis
Websites: Dong Group
Contact: gbdong@uchicago.edu
(773) 834-0396
Assistant: Alia McDaniel
Office Location:
Room SCL 428, Searle Chemical Laboratory, 5735 S Ellis Ave, Chicago, IL 60637

C–C Bond Activation

Our long-term goal is to greatly extend the regime of C−C activation to a wide range of organic compounds and enable synthetically useful transformations.

“Cut & Sew”: Bridged/fused rings can be accessed by employing a transition metal to first regioselectively cleave a cyclic C–C bond, followed by an intramolecular insertion of an unsaturated bond, and finally, reductive elimination to afford the desired ring system. Such a “Cut & Sew” sequence would result in reorganization of bond connections and lead to novel molecular structures with high complexity. We expect that, by changing ring-sizes, linker-lengths and unsaturated unit-types, a great diversity of scaffolds that are difficult to access by conventional methods would be afforded using a single approach.
Less strained ketones: Recently, progress has been made for C−C activation of common unstrained ketones, such as cyclopentanones, cyclohexanones and linear ketones.
Cleavage of Unstrained Aryl-Aryl Bonds.We have developed a general approach for catalytic activation of the unstrained C(aryl)−C(aryl) bonds in 2,2’-biphenols.

Byproduct-Free Ketone Alkylation

Alkylation of carbonyl compounds is one very important way to form carbon-carbon bonds. Conventionally, toxic and expensive alkyl halides are employed as alkylating agents in combination with strong basic conditions, typically generating stoichiometric halogen-containing byproducts during reactions.We developed a bifunctional catalytic system that utilizes enamine-transition metal cooperative interactions to enable direct ketone alkylation with simple olefins as the alkylating agents.

Non-Directed β-Functionalization of Carbonyl Compounds

Conventionally, β-C−C forming reactions largely rely on conjugate addition of a soft nucleophile (e.g. organocuprates) to an α,β-unsaturated carbonyl substrate (e.g. conjugated enones) with or without a transition-metal (TM) catalyst. While effective, this approach typically requires unsaturated carbonyls and metalated nucleophiles. A Pd-catalyzed redox cascade approach has been developed, which can directly functionalize the β-position of carbonyl compounds. This approach merges Pd-catalyzed desaturation, C−X bond activation and conjugate addition.

Exo-type Directing Group for Site-selective C−H Activation

To achieve site-selective functionalization of unactivated aliphatic C−H bonds in alcohols and amines, we are exploring a new class of exo-type directing groups (DGs) that can be easily installed and removed from alcohol and amine substrates. In addition, we have illustrated the use of a temporary and catalytic exo-DG in direct γ and δ-arylation of free amines.

Palladium/Norbornene Catalysis

Palladium/norbornene (Pd/NBE) cooperative catalysis, also known as the Catellani-type reactions, holds promise for streamlining synthesis of poly-substituted arenes, as it can directly couple an electrophile as the ortho position and a nucleophile at the ipso position of arene simultaneously. In the past, the applicability of this method has been largely hampered by three constraints: 1) the type of electrophiles that can be employed as previously only alkyl and certain aryl electrophiles could be used; 2) the use of aryl iodides as substrates (as use of more readily available aryl bromides was generally not effective); and 3) the requirement of an ortho substituent on aryl-halides for mono ortho functionalization. Since 2012, efforts have been made here to address these constraints through in-depth mechanistic understanding, including discoveries of new classes of electrophiles, new ligand systems and new norbornene cofactors.

Total Synthesis and Drug Discovery

We have been interested in synthesis of structurally complex and biologically important natural products, specifically those with potent anti-cancer and immunosuppressive properties. Our long-term goal is to understand their mechanism of action and structure-activity relationship to ultimately facilitate drug discovery.

Polymer Chemistry

We have been interested in developing new polymerization approaches to prepare functionalized polymers. Utilizing the power of palladium/norbornene catalysis, we have developed an in situ-functionalization strategy, namely an A2B2C polymerization, for preparing poly-substituted aromatic polymers.

The University of Chicago
Professor of Chemistry
Present

CPRIT Scholar for Cancer Research, University of Texas at Austin
Assistant Professor
2016

California Institute of Technology
Camille and Henry Dreyfus Postdoctoral Fellow
2011

Stanford University
Ph.D. - Chemistry
2009

Peking University
Beijing, China

2003

Zhang, Rui; Yu, Tingting and Dong, Guangbin* “Rhodium catalyzed tunable amide homologation through a hook-and-slide strategy” Science 2023, 382, 951-957. https://www.science.org/stoken/author-tokens/ST-1563/full;

Wu, Zhao; Xu, Xiaolong; Wang, Jianchun and Dong, Guangbin* “Carbonyl 1,2-transposition through triflate-mediated α-amination” Science 2021, 374, 734-740. https://www.science.org/stoken/author-tokens/ST-140/full

Zhu, Jun‡.; Zhang, Rui‡ and Dong, Guangbin* “Orthogonal cross-coupling through intermolecular metathesis of unstrained C(aryl)–C(aryl) single bonds” Nat. Chem. 2021, 13, 836-842. https://www.nature.com/articles/s41557-021-00757-4

Wang, Jianchun; Li, Renhe; Dong, Zhe; Liu, Peng; and Dong, Guangbin* “Complementary site-selectivity in arene functionalization enabled by overcoming the ortho constraint in palladium/norbornene catalysis” Nat. Chem. 2018, 10, 866-872. https://www.nature.com/articles/s41557-018-0074-z;

Xia, Ying; Lu, Gang; Liu, Peng; and Dong, Guangbin.* “Catalytic Activation of Carbon–carbon Bonds in Cyclopentanones” Nature, 2016, 539, 546. https://www.nature.com/articles/nature19849;

Mo, Fanyang; Dong, Guangbin.* “Regioselective ketone α-alkylation with simple olefins via dual activation”. Science, 2014, 345, 68–72. https://www.science.org/doi/10.1126/science.1254465?ijkey=oCdhkrWqF4%2FV6&keytype=ref&siteid=sci

Huang, Zhongxing; Dong, Guangbin.* “Catalytic Direct β-Arylation of Simple Ketones with Aryl Iodides”. J. Am. Chem. Soc. 2013, 135, 17747-17750. https://pubs.acs.org/doi/full/10.1021/ja410389a

Xu, Tao; Dong, Guangbin.* “Rh-Catalyzed Regioselective Carboacylation of Olefins: A C-C Activation Approach to Access Fused-Ring Systems.” Angew. Chem., Int. Ed. 2012, 51, 7567. https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201202771

Mukaiyama Award
Society of Synthetic Organic Chemistry, Japan
2025

Mitsui Chemicals Catalysis Science Awards
2024

Fellow
American Association for the Advancement of Science
2024

Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator
2024

Zen-Ichi Yoshida Lectureship
International Organic Chemistry Foundation
2023

Finalist
Blavatnik National Awards for Young Scientists
2022

Arthur C. Cope Scholar Award
2017

American Cancer Society Research Scholar
2014

Amgen Young Investigators’ Award
2014

Dupont Young Professor Program Award
2014

Teaching Excellent Award, UT Austin
2014

CAPA Biomatik Distinguished Junior Faculty Award
2014