Powerful Partners: Ionic Promoters and the Enantioselective Heck-Matsuda Reaction

• Grant number: 17/01779-2
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• Start date: June 01, 2017
• End date: May 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Ricardo Almir Angnes
• Supervisor: Gerald Bruce Hammond
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: University of Louisville (UofL), United States
• Associated to the scholarship: 13/25849-9 - Application of the enantioselective Heck-Matsuda reaction for substrate oriented regioselective desymmetrizations, BP.DR

Abstract

Considering the expertise of both research groups involved in this project, we propose the development of new enantioselective Heck-Matsuda (EHM) reactions and cascade processes taking advantage of reagents developed by the Hammond's group.In one instance, we plan to use the ionic promoter KCTf3 for the development of a substrate-directed EHM arylation of meso (1R,2S)-cyclohex-4-ene-1,2-diol. This methodology can lead to highly functionalized building blocks that are present as a substructure in a variety of biologically active compounds and natural products like pancrastatin.Another objective of this project is the EHM arylation/functionalization cascade of substituted cyclopropenes. Herein we want to take advantage of a series of fluorination reagents developed at the hosting lab. This procedure can give direct access to pyrethroid analogues, an important class of insecticides.

Scientific publications

(4)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

ANGNES, RICARDO A.; POTNIS, CHINMAY; LIANG, SHENGZONG; CORREIA, CARLOS ROQUE D.; HAMMOND, GERALD B.. Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C-N Bond Formation with Alkyl Radicals. Journal of Organic Chemistry, v. 85, n. 6, p. 4153-4164, MAR 20 2020. (17/01779-2, 13/25849-9, 14/25770-6)

LIANG, SHENGZONG; KUMON, TATSUYA; ANGNES, RICARDO A.; SANCHEZ, MELISSA; XU, BO; HAMMOND, GERALD B.. Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation. ORGANIC LETTERS, v. 21, n. 10, p. 3848-3854, MAY 17 2019. (17/01779-2)

ANGNES, RICARDO A.; THOMPSON, LEE M.; MASHUTA, MARK S.; CORREIA, CARLOS R. D.; HAMMOND, GERALD B.. Non-Covalent Substrate Directed Enantioselective Heck Desymmetrization of cis-Cyclohex-4-ene-1,2-diol: Synthesis of all cis Chiral 5-Aryl-cyclohex-3-ene-1,2-diols and Mechanistic Investigation. ADVANCED SYNTHESIS & CATALYSIS, v. 360, n. 19, p. 3760-3767, OCT 4 2018. (17/01779-2, 13/25849-9, 14/25770-6)

LIANG, SHENGZONG; ANGNES, RICARDO A.; POTNIS, CHINMAY S.; HAMMOND, GERALD B.. Photoredox catalyzed C(sp(3))-C(sp) coupling of dihydropyridines and alkynylbenziodoxolones. Tetrahedron Letters, v. 60, n. 45, NOV 7 2019. (17/01779-2)