Synthesis of Naphthalene‐ and Phenanthrene‐Fused Smaragdyrins and Their BF2 Complexes

Author:

Liu Pingting1,Wang Kaisheng1,Xu Ling1,Rao Yutao1,Zhou Mingbo1,Osuka Atsuhiro1,Song Jianxin1ORCID

Affiliation:

1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China) Key Laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province College of Chemistry and Chemical Engineering Hunan Normal University Changsha 410081 China

Abstract

AbstractNaphthalene‐ and phenanthrene‐fused [22]smaragdyrin BF2‐complexes were synthesized by 1) Suzuki‐Miyaura coupling of β‐brominated [22]smaragdyrin BF2 complexes with 2‐formylarylboronates, 2) Witting‐type methoxymethylenation of the formyl group, and 3) methanesulfonic acid‐catalyzed cyclization reaction. Subsequently these BF2 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 BF2 complexes and the antiaromatic characters of the [20]smaragdyrin free bases.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Biochemistry,Organic Chemistry

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