Synthesis of Substituted Bacteriochlorins
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Date
2010-04-22
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Abstract
The objective of this work is two-fold: first, to find new conditions to improve the condensation reactions leading to the macrocycles 3,13-dibromo-5-methoxybacteriochlorin (BC-Br3OMe5Br13) and 3,13-dibromobacteriochlorin (BC-Br3Br13), and second, to functionalize the valuable BC-Br3OMe5Br13 building block. This work improves upon past condensation methods, which afforded low yields of bacteriochlorin with an inseparable chlorin product during formation of BC-Br3Br13, and provided no access to BC-Br3OMe5Br13.
Through microscale optimization of conditions, solvents, concentrations, Lewis acids, and additives, BC-Br3OMe5Br13 and BC-Br3Br13 were isolated in 42% and 30% yield, respectively.
Several derivatizations including diacetylation of BC-Br3OMe5Br13 was achieved in 70% yield, followed by bromination at the β-position in 22% yield. Stille coupling of BC-Br3OMe5Br13 to introduce a formyl group was performed in 30% yield. Two TIPS-ethynyl groups were also installed on BC-Br3OMe5Br13 in 4.7% yield.
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Keywords
porphyrin, bacteriochlorin, chlorin
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Degree
MS
Discipline
Chemistry
