Central zinc metal-controlled regioselective meso-bromination of zincated β-silylporphyrins—rapid access to meso, β-dual-functionalized porphyrins. Issue 48 (8th December 2020)

• Record Type: Journal Article
• Authors: Hayashi, Satoshi; Takamatsu, Rina; Takeda, Shiori; Noji, Masahiro; Takanami, Toshikatsu
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 48(2020)
• Page Start: 9791
• Page End: 9795
• Publication Date: 2020-12-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob02262d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A convenient method for preparing meso, β-dual-functionalized porphyrin through a central zinc metal-controlled regioselective bromination of zincated β-silylporphyrin was developed. Abstract : A convenient method for the preparation of meso, β-dual-functionalized porphyrin was developed. The bromination of zincated β-silylporphyrin with NBS selectively yielded meso -bromo-β-silylporphyrin, whereas, the bromination of free-base β-silylporphyrin selectively yielded β-bromoporphyrin via an ipso -substitution of the silyl group. These meso, β-dual-functionalized porphyrins could be used as multipurpose synthons for fabricating various porphyrin derivatives.