Palladium-catalyzed cyanation of porphyrins utilizing cyanoethylzinc bromide as an efficient cyanide ion source

Organic Letters

Volumn 7, Issue 18, 2005, Pages 3937-3940

  Takanami, Toshikatsu ^a   Hayashi, Mikiko ^a   Chijimatsu, Hiroshi ^a   Inoue, Wakaba ^a   Suda, Kohji ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944506824     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514294     Document Type: Article

References (46)

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7. The following four methods have been reported for the cyanation of porphyrins: (i) classic Rosemund-von Braun cyanation reactions with stoichiometric copper(I) cyanide at elevated temperatures (see ref 5); (ii) a multiple-step procedure involving Vilsmeier formylation, oxime formation, and dehydration (see ref 6); (iii) nucleophilic addition of cyanide ion to the π-cation radical of porphyrins (see ref 7); and (iv) Friedel-Crafts cyanation of porphyrins with cyanogen bromide/aluminum chloride (see ref 8). These reactions, other than Rosemund-von Braun cyanation, involve cationic porphyrin intermediates and, hence, can hardly be applied towards the preparation of porphyrins bearing more than one nitrile group: the introduction of a CN group deactivates the system toward further cyanation.
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35. 6] are typically used as a cyanide ion source in the catalytic cyanation of aryl halides: (a) Yang, C.; Williams, M. Org. Lett. 2004, 6, 2837-2840.
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41. Only the debrominated product [5,15-diphenylporphinato]zinc(II) was isolated as a byproduct.
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46. 4 in THF at 40°C, giving essentially the same result as that obtained from the reaction performed at 60°C (cf. entry 1 in Table 1), affording the corresponding cyanated product 3a (41%), though a longer reaction time (12 h) was necessary to complete the reaction. Thus, another reactive metallic-cyano species seems not to be formed from degradation of cyanoethylzinc bromide 2 in the catalytic process under the present reaction conditions.