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Synthesis of Naphthalene- and Phenanthrene-Fused Smaragdyrins and Their BF 2 Complexes.

Authors :
Liu P
Wang K
Xu L
Rao Y
Zhou M
Osuka A
Song J
Source :
Chemistry, an Asian journal [Chem Asian J] 2023 Nov 02; Vol. 18 (21), pp. e202300740. Date of Electronic Publication: 2023 Sep 21.
Publication Year :
2023

Abstract

Naphthalene- and phenanthrene-fused [22]smaragdyrin BF <subscript>2</subscript> -complexes were synthesized by 1) Suzuki-Miyaura coupling of β-brominated [22]smaragdyrin BF <subscript>2</subscript> complexes with 2-formylarylboronates, 2) Witting-type methoxymethylenation of the formyl group, and 3) methanesulfonic acid-catalyzed cyclization reaction. Subsequently these BF <subscript>2</subscript> complexes were deboronized and oxidized to the corresponding antiaromatic [20]smaragdyrin free bases. The installed fused structures led to decrease of the aromatic characters of the [22]smaragdyrin BF <subscript>2</subscript> complexes and the antiaromatic characters of the [20]smaragdyrin free bases.<br /> (© 2023 Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1861-471X
Volume :
18
Issue :
21
Database :
MEDLINE
Journal :
Chemistry, an Asian journal
Publication Type :
Academic Journal
Accession number :
37712306
Full Text :
https://doi.org/10.1002/asia.202300740