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

Grant number: 17/01779-2
Support type:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): June 01, 2017
Effective date (End): May 31, 2018
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Carlos Roque Duarte Correia
Grantee:Ricardo Almir Angnes
Supervisor abroad: Gerald Bruce Hammond
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
Research place: 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.

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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. Web of Science Citations: 0.
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. Web of Science Citations: 1.
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. Web of Science Citations: 1.
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. Web of Science Citations: 5.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.