Aryne‐Based Synthesis of Cyclobutadiene‐Containing Oligoacenes and Related Extended Biphenylene Derivatives

Author:

Álvarez Berta12,Janeiro Jesús12,Cobas Agustín2,Ortuño Manuel A.1,Peña Diego12,Guitián Enrique12,Pérez Dolores12ORCID

Affiliation:

1. Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS) Universidade de Santiago de Compostela. 15782- Santiago de Compostela Spain

2. Departamento de Química Orgánica Universidade de Santiago de Compostela. 15782- Santiago de Compostela Spain

Abstract

AbstractA previously undescribed aryne derived from a π‐extended biphenylene, 2,3‐didehydrobenzo[b]biphenylene, has been developed. The participation of this new aryne building block in [4+2] and palladium‐catalyzed [2+2+2] cycloaddition reactions has been applied to the synthesis of a variety of polycyclic conjugated hydrocarbons (PCHs) with appealing structures which combine (aromatic) benzene and (antiaromatic) cyclobutadiene (CBD) rings. Among them, a family of unsubstituted (or barely substituted) CBD‐oligoacenes has been accessed by iterative Diels‐Alder reactions of the new aryne with furans and/or isobenzofurans, followed by deoxygenative aromatization of the resulting epoxy‐derivatives. The experimental and computational studies of the newly synthesized PCHs suggest an important degree of electron delocalization along the polycyclic skeleton, more pronounced in the linearly fused derivatives. The computed ACID plots reveal clockwise current density vectors at the peripheral bonds, originating from the σ contributions of the antiaromatic cyclobutadiene rings.

Funder

Xunta de Galicia

Publisher

Wiley

Subject

General Chemistry

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