Abstract

We are interested in developing general and useful new methods for the formation of carbon- carbon and carbon-heteroatom bonds. Utilizing copper-catalysis we will focus on the direct asymmetric functionalization of benzimidazoles with unactivated olefins. Substituted benzimidazoles are ubiquitous scaffolds in pharmaceuticals, natural products, agrochemicals, electronics and sensors. New methods would allow access to quickly and efficiently build a wide-range of complex molecules. Optimization of reaction conditions, exploration of substrate scope and mechanistic studies will be conducted to aid us in the discovery and utility of this work.

Public Health Relevance

We are interested in developing general and useful new methods for the asymmetric functionalization of nitrogen heterocycles. These scaffolds are important structures found in many biologically relevant compounds. Mechanistic studies will aid us in the design, optimization, and application of these techniques and further our understanding of metal- catalyzed processes.

  Funding Agency

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Unknown (R35)
Project #
3R35GM122483-03S1
Application #
9923326
Study Section
Special Emphasis Panel (ZGM1)
Program Officer
Yang, Jiong
Project Start
2017-06-01
Project End
2022-05-31
Budget Start
2019-06-01
Budget End
2020-05-31
Support Year
3
Fiscal Year
2019
Total Cost
Indirect Cost

  Institution

Name
Massachusetts Institute of Technology
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
001425594
City
Cambridge
State
MA
Country
United States
Zip Code
02142

  Publications

Dennis, Joseph M; White, Nicholas A; Liu, Richard Y et al. (2018) Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling. J Am Chem Soc 140:4721-4725
Tsai, Erica Y; Liu, Richard Y; Yang, Yang et al. (2018) A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes. J Am Chem Soc 140:2007-2011
Liu, Richard Y; Buchwald, Stephen L (2018) Copper-Catalyzed Enantioselective Hydroamination of Alkenes. Organic Synth 95:80-96
Zhang, Hong; Ruiz-Castillo, Paula; Buchwald, Stephen L (2018) Palladium-Catalyzed C-O Cross-Coupling of Primary Alcohols. Org Lett 20:1580-1583
Kubota, Koji; Dai, Peng; Pentelute, Bradley L et al. (2018) Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking. J Am Chem Soc 140:3128-3133
Liu, Richard Y; Bae, Minwoo; Buchwald, Stephen L (2018) Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes. J Am Chem Soc 140:1627-1631
Zhou, Yujing; Bandar, Jeffrey S; Liu, Richard Y et al. (2018) CuH-Catalyzed Asymmetric Reduction of ?,?-Unsaturated Carboxylic Acids to ?-Chiral Aldehydes. J Am Chem Soc 140:606-609
Ichikawa, Saki; Zhu, Shaolin; Buchwald, Stephen L (2018) A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination. Angew Chem Int Ed Engl 57:8714-8718
Gribble Jr, Michael W; Guo, Sheng; Buchwald, Stephen L (2018) Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile. J Am Chem Soc 140:5057-5060
Zhou, Yujing; Engl, Oliver D; Bandar, Jeffrey S et al. (2018) CuH-Catalyzed Asymmetric Hydroamidation of Vinylarenes. Angew Chem Int Ed Engl 57:6672-6675

Showing the most recent 10 out of 18 publications