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The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines
(Canadian Journal of Chemistry, 2014)
Benzyl esters are cleaved upon reaction with SnCl4, resulting in isolation of the corresponding carboxylic acid. Importantly, benzyl ethers, amines and amides do not undergo debenzylation under these conditions, nor do a ...
Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles
(Canadian Journal of Chemistry, 2018)
The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through the adoption of two mechanistic pathways. The key ...
Synthesis of symmetric meso-H dipyrrin hydrobromides from 2-formyl pyrroles
(Synlett, 2014)
The reaction of 2-formyl pyrroles in acidic methanol gives the corresponding symmetric, meso-H 4,6-dipyrrin hydrobromides. This convenient strategy involves initial deformylation under the acidic conditions, followed by ...
Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts
(Chemical Communications, 2018)
We report the lithium, sodium and potassium salts of aza-dipyrrins and detail their use as anionic aza-dipyrrinato ligand sources in complexation. Of the three types of alkali salts studied, those of lithium are found to ...
Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties
(Canadian Journal of Chemistry, 2015)
The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes ...
Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes
(2019)
Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the ...
Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands
(2019)
A parameter is reported by which to use 13C NMR chemical shifts to measure and predict the donor capabilities of N^N dipyrrinato and aza-dipyrrinato ligands chelating in L^X fashion. The results enable the rationalisation ...
The Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
(2019)
The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate
esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction
proceeds via intramolecular ...
Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
(RSC Advances, 2019)
2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach ...
Facile Deprotection of F-BODIPYs using Methylboronic Acid
(2020)
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) are deprotected through removal of
the –BF2 moiety upon treatment with methylboronic acid. The tolerance of various substitution
patterns about the dipyrrinato core ...