| Regioselective 15-bromination and functionalization of a stable synthetic bacteriochlorin. | |
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MedLine Citation:
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PMID: 17567079 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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5-Methoxy-8,8,18,18-tetramethyl-2,12-di-p-tolylbacteriochlorin (MeO-BC) undergoes regioselective electrophilic bromination with NBS to give the 15-bromo analogue (MeO-BC-Br15) in 85% yield. By contrast, the bacteriochlorin lacking the 5-methoxy group (8,8,18,18-tetramethyl-2,12-di-p-tolylbacteriochlorin, H-BC) gives a mixture of two monobromo- and two dibromobacteriochlorins. Deuterium exchange of both bacteriochlorins (H-BC and MeO-BC) in acidic media (TFA-d) occurs preferentially at the beta-pyrrole positions (3, 13) > unhindered meso-positions (5, 15 for H-BC; 15 for MeO-BC) > hindered meso-positions (10, 20). The 15-bromo-5-methoxybacteriochlorin MeO-BC-Br15 was subjected to three types of Pd-mediated coupling reactions (Suzuki, Sonogashira, Hartwig-Buchwald) to give six bacteriochlorins bearing functional groups at the 15-position (49% to 85% yield). The groups include 4-(tert-butoxycarbonylmethoxy)phenyl, 4-pyridyl, 3,5-diformylphenyl, phenylethynyl, TIPS-ethynyl, and N-benzamido. The presence of the 15-ethynyl moiety shifts the position of the long-wavelength Qy band from 732 nm to approximately 753 nm. The ability to introduce a range of groups at a specific site enables synthetic bacteriochlorins to be tailored for a variety of applications. |
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Authors:
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Dazhong Fan; Masahiko Taniguchi; Jonathan S Lindsey |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2007-06-13 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Jul |
Date Detail:
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Created Date: 2007-06-29 Completed Date: 2007-08-13 Revised Date: 2010-09-16 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5350-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Bromine
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chemistry* Deuterium Exchange Measurement Magnetic Resonance Spectroscopy Molecular Structure Palladium / chemistry Porphyrins / chemical synthesis*, chemistry Spectrophotometry Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM36238/GM/NIGMS NIH HHS; R01 GM036238-19/GM/NIGMS NIH HHS; R01 GM036238-20/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Porphyrins; 0/bacteriochlorin; 7440-05-3/Palladium; 7726-95-6/Bromine |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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