期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 1, 页码 275-285出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo048440m
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资金
- NIGMS NIH HHS [GM36238] Funding Source: Medline
Chlorins/oxochlorins bearing distinct patterns of substituents are valuable compounds in bioorganic and materials chemistry. Treatment of a 5,10-diaryl-substituted chlorin or oxochlorin with TFA-d(1) resulted in selective deuteriation of the remaining meso positions (15, 20) rather than any of the beta-pyrrolic positions. Electrophilic iodination or bromination of a 5,10-diaryl-substituted chlorin proceeded with high regioselectivity, affording the 5,10-diaryl-15-halo-substituted chlorin. Iodination or bromination of a free base 5,10-diaryloxochlorin gave a mixture of products arising through halogenation at the 15-, 20-, and beta-pyrrolic positions, while bromination of a zinc 5,10-diaryloxochlorin selectively gave the 5,10-diaryl-20-bromo-substituted oxochlorin. The Suzuki coupling reaction of a phenyl boronic acid derivative and a 5,10-diaryl-15-iodooxochlorin or 5,10-diaryl-20-bromooxochlorin gave the corresponding 5,10,15- or 5,10,20-triaryloxochlorin. The introduction of a third aryl substituent into the chlorin or oxochlorin causes an similar to5-nm red shift of the long wavelength Q(y) absorption band. Two phenylethyne-linked oxochlorin-oxochlorin dyads in distinct metalation states (zinc/free base, free base/zinc) were prepared by Sonogashira coupling reactions of a 5,10-diaryl-20-bromooxochlorin and a 10-substituted ethynylphenyl oxochlorin. This study provides access to new chlorins/oxochlorins that can be utilized in diverse applications.
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