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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Rapid Synthesis of Alkyloxy Porphyrins Under Microwave Irradiation

, , , , &
Pages 20-28 | Received 11 Jan 2008, Published online: 15 Feb 2011
 

Abstract

Alkyloxy porphyrins have been prepared by direct coupling of 5-para-hydroxyphenyl-10,15,20-triphenylporphyrin and alkyl halides under microwave irradiation within several minutes. The length of the alkyl halides has no obvious effect on the yields and reaction time; however, the steric structure of the alkyl halides has a great impact on the reaction time. All the products were confirmed by 1H NMR.

ACKNOWLEDGMENTS

The authors thank the prophase research of National Key Basic Research Development Plan of China (2005CCA01400), the National Natural Science Foundation of China (20776053), and the Program for New Century Excellent Talents in University (NCET-06–740) for providing financial support for this project.

Notes

a Reaction conditions: 0.16 mmol (0.1 g) HOPTPP, 1.6 mmol dodecyl bromide, 20 mL DMF, 2 g anhydrous K2CO3, 3 min.

b All yields refer to isolated product which were characterized by 1H NMR data.

c Reaction conditions: 8 mL DMF, 5.0 mmol (2 g) NaOH, 0.179 mmol (0.113 g) HOPTPP, 0.458 mmol (0.114 g) dodecyl bromide, room temperature, 3 h.

a Reaction conditions: 0.16 mmol (0.1 g) HPTPP, 1.6 mmol alkyl halide, 20 mL DMF, and 2 g anhydrous K2CO3, 300 W power.

b All yields refer to isolated products, which were characterized by1H NMR data.

c Reaction conditions: 4.3 mmol (2.73 g) HOPTPP, 100 mL DMF, 0.065 mol (14 g) 1, 4-dibromobutane, 9 g anhydrous K2CO3, room temperature, 36 h.

d 8 mL DMF, 0.2 g (5.0 mmol) NaOH, 0.1 13 g (0.179 mmol) HOPTPP,0.114 g (0.458 mmol) of dodecyl bromide, room temperature, 3 h.

e 0.25 mmol (0.158 g) HOPTPP, 30 mL DMF, 80.°C, 1 mL hexadecyl bromide, 3 h.

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