... 10. No evidence for oxidation at C8C9 was observed by examination of crude NMR mixtures and a... more ... 10. No evidence for oxidation at C8C9 was observed by examination of crude NMR mixtures and analysis of the product profile after diol cleavage. 11. Baskaran, S.;Chandrasekaran, S. Tetrahedron Lett. 1990, 31, 2775. The ...
Two short topics were presented in the lecture titled Some Highlights of an Agro Career presented... more Two short topics were presented in the lecture titled Some Highlights of an Agro Career presented at the Fall Meeting Swiss Chemical Society, September 10th, 2021. The first of these topics discussed the discovery of the selective corn herbicide Bicyclopyrone. The second topic presented was concerned with host marking pheromones (HMPs), and described the HMP of the Mexican fruit fly anastrepha ludens, and its use in crop protection. The story concerning the host marking pheromones of the Mexican fruit fly has already been published in this journal[1] and thus this review will describe the discovery of Bicyclopyrone.
In this review, the synthesis of 33 agrochemicals that received an international standardization ... more In this review, the synthesis of 33 agrochemicals that received an international standardization organization (ISO) name between January 2015 and December 2018 is described. The aim is to showcase the broad range and scope of reactions, reagents and intermediates used to discover and produce the latest active ingredients addressing the crop protection industry's needs.
The ruthenium(II) bis(PYA) complex 1 (PYA = p-pyridylidene amide) is a powerful catalyst for the ... more The ruthenium(II) bis(PYA) complex 1 (PYA = p-pyridylidene amide) is a powerful catalyst for the oxidation of sulfides to sulfones, of alkenes to carbonyl compounds, and of terminal alkynes to carboxylic acids by using NaIO4 as the terminal oxidant. The catalytic system shows a broad functional group tolerance and rate differences between alkyne and sulfide oxidation that are sufficiently large to effectively achieve selective sulfide oxidation with exquisite selectivity.
Chemical science (Royal Society of Chemistry : 2010), 2013
C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmace... more C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmaceuticals. C-3 C-H arylation of (1H) indazole and pyrazole has been a significant challenge due to the poor reactivity of the C-3 position. Herein, we report a practical Pd(II)/Phen catalyst and conditions for direct C-3 arylation of indazole and pyrazole with ArI or ArBr without using Ag additives as halide scavengers. The use of toluene, chlorobenzene, trifluoromethylbenzene and mesitylene as the solvent was found to be crucial for the selectivity and reactivity. We further demonstrate the robustness of this protocol through the first total synthesis of Nigellidine hydrobromide as well as expedient preparation of heterocycles structurally related to pesticides and drug molecules.
The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporate... more The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporated into molecules with useful biological properties. During the period 1990-2017 (September) fourteen crop protection products bearing a trifluoromethyl pyridine have been commercialized or proposed for an ISO common name, covering fungicides, herbicides, insecticides and nematicides. Chemical processes have been developed to provide trifluoromethyl pyridine intermediates, from non-fluorinated pyridine starting materials, at scale and with affordable costs of goods. These attractive starting materials were then readily adopted by research chemists, and elaborated through simple chemical modifications into new active ingredients. In a second approach, substituted trifluoromethyl pyridine rings have been constructed from acyclic, trifluoromethyl starting materials, which again has served to identify new active ingredients. Molecular matched pair analysis will reveal subtle, yet important di...
... 10. No evidence for oxidation at C8C9 was observed by examination of crude NMR mixtures and a... more ... 10. No evidence for oxidation at C8C9 was observed by examination of crude NMR mixtures and analysis of the product profile after diol cleavage. 11. Baskaran, S.;Chandrasekaran, S. Tetrahedron Lett. 1990, 31, 2775. The ...
Two short topics were presented in the lecture titled Some Highlights of an Agro Career presented... more Two short topics were presented in the lecture titled Some Highlights of an Agro Career presented at the Fall Meeting Swiss Chemical Society, September 10th, 2021. The first of these topics discussed the discovery of the selective corn herbicide Bicyclopyrone. The second topic presented was concerned with host marking pheromones (HMPs), and described the HMP of the Mexican fruit fly anastrepha ludens, and its use in crop protection. The story concerning the host marking pheromones of the Mexican fruit fly has already been published in this journal[1] and thus this review will describe the discovery of Bicyclopyrone.
In this review, the synthesis of 33 agrochemicals that received an international standardization ... more In this review, the synthesis of 33 agrochemicals that received an international standardization organization (ISO) name between January 2015 and December 2018 is described. The aim is to showcase the broad range and scope of reactions, reagents and intermediates used to discover and produce the latest active ingredients addressing the crop protection industry's needs.
The ruthenium(II) bis(PYA) complex 1 (PYA = p-pyridylidene amide) is a powerful catalyst for the ... more The ruthenium(II) bis(PYA) complex 1 (PYA = p-pyridylidene amide) is a powerful catalyst for the oxidation of sulfides to sulfones, of alkenes to carbonyl compounds, and of terminal alkynes to carboxylic acids by using NaIO4 as the terminal oxidant. The catalytic system shows a broad functional group tolerance and rate differences between alkyne and sulfide oxidation that are sufficiently large to effectively achieve selective sulfide oxidation with exquisite selectivity.
Chemical science (Royal Society of Chemistry : 2010), 2013
C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmace... more C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmaceuticals. C-3 C-H arylation of (1H) indazole and pyrazole has been a significant challenge due to the poor reactivity of the C-3 position. Herein, we report a practical Pd(II)/Phen catalyst and conditions for direct C-3 arylation of indazole and pyrazole with ArI or ArBr without using Ag additives as halide scavengers. The use of toluene, chlorobenzene, trifluoromethylbenzene and mesitylene as the solvent was found to be crucial for the selectivity and reactivity. We further demonstrate the robustness of this protocol through the first total synthesis of Nigellidine hydrobromide as well as expedient preparation of heterocycles structurally related to pesticides and drug molecules.
The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporate... more The pyridine ring, substituted by a trifluoromethyl substituent has been successfully incorporated into molecules with useful biological properties. During the period 1990-2017 (September) fourteen crop protection products bearing a trifluoromethyl pyridine have been commercialized or proposed for an ISO common name, covering fungicides, herbicides, insecticides and nematicides. Chemical processes have been developed to provide trifluoromethyl pyridine intermediates, from non-fluorinated pyridine starting materials, at scale and with affordable costs of goods. These attractive starting materials were then readily adopted by research chemists, and elaborated through simple chemical modifications into new active ingredients. In a second approach, substituted trifluoromethyl pyridine rings have been constructed from acyclic, trifluoromethyl starting materials, which again has served to identify new active ingredients. Molecular matched pair analysis will reveal subtle, yet important di...
Uploads
Papers by Andrew Edmunds