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Volumn , Issue 14, 2008, Pages 2147-2149

A 'click' chemistry route to 'capped' porphyrins

Author keywords

1,2,3 triazoles; 1,3 dipolar cycloaddition; Alkyne; Azide; Porphyrin

Indexed keywords

1.2.3 TRIAZOLE; N,N DIMETHYLFORMAMIDE; PORPHYRIN DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 51149094996 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077899 Document Type: Article

Times cited : (15)

References (16)

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- Almog, J.¹ Baldwin, J.E.² Crossley, M.J.³ Debernadis, J.F.⁴ Dyer, R.L.⁵ Huff, J.R.⁶ Peters, M.K.⁷

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11
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- 3): δ = 164.9, 133.9, 130.1, 76.7, 76.0, 53.8.
- 3): δ = 164.9, 133.9, 130.1, 76.7, 76.0, 53.8.

12
- 51149121050
- Tetrahydrofuran-H2O Method for the Cycloaddition: To a stirred mixture of porphyrin 5 (65 mg) and Et3N (40 μL) in THF (100 mL) were added CuSO4·5H2O (4 mg) and ascorbic acid (5 mg) dissolved in H2O (15 mL, Then a solution of tetraalkyne 4 in THF (35 mL) was added and the mixture was heated at reflux for 24 h. An additional portion of CuSO4·5H2O (4 mg) and L-ascorbic acid (5 mg) in H2O (5 mL) was added and refluxed for a further 6 h. The reaction was then filtered, evaporated to approximately 20 mL with CH2Cl2 (100 mL) and H2O (100 mL) added. The organic phase was collected and the aqueous phase was extracted with a mixture of MeOH and H2O 1:1, 2 x 100 mL, This was then dried over Na2SO4, filtered and evaporated. Purification on silica with 4% MeOH in H2O yielded capped porphyrin 3
- 2O yielded capped porphyrin 3 in 19% yield.

13
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- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 8235
- Lipshutz, B.H.¹ Taft, B.R.²

15
- 51149090652
- Dimethylformamide Method for the Cycloaddition: To a stirred solution of 5 (45 mg, NCCH3)4CuPF6 (4 mg) and Et3N (28 μL) in DMF (100 mL) was added 4 (20 mg, This was then put under nitrogen and stirred at 70°C for 16 h. This was then added to a mixture of CH2Cl2 and EtOAc (1:1, 200 mL, washed with H2O (2 x 100 mL, and the organic phase was filtered and washed again with H2O 2 x 100 mL, The organic phase was then dried over Na2SO4, filtered and evaporated with the residue subjected to purification on silica, eluting capped porphyrin 3 in 14% yield
- 4, filtered and evaporated with the residue subjected to purification on silica, eluting capped porphyrin 3 in 14% yield.

16
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- Cross, K.J.¹ Crossley, M.J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.