Preparation of Hetero‐π‐Conjugated Compounds by Double Nucleophilic Addition to Haloalkynes and C−H Cyclization

Author:

Hata Takeshi1ORCID,Tatsumi Yuta1,Kanai Yuki1,Takahashi Naoto1,Shigeta Masayuki1,Urabe Hirokazu12

Affiliation:

1. Department of Life Science and Technology School of Life Science and Technology Tokyo Institute of Technology 4259-B-59 Nagatsuta-cho Midori-ku, Yokohama Kanagawa 226–8501 Japan

2. Present address: Department of Applied Chemistry Meiji University 1-1-1 Higashimita Tama-ku, Kawasaki Kanagawa 214-8571 Japan

Abstract

AbstractWhen a mixture containing 1‐halo‐1‐alkyne, a dinucleophilic agent, and a base (Cs2CO3 or K3PO4) was heated in DMF, regio‐ and stereo‐selective nucleophilic addition of the dinucleophilic agent to the acetylenes occurred. This reaction yielded (Z,Z)‐bis(haloalkene), which subsequently underwent Pd‐catalyzed cyclization through C−H bond activation, resulting in the formation of two‐oxygen‐ or ‐nitrogen‐containing hetero‐π‐conjugated compounds. N‐(5‐Hydroxynaphthalen‐1‐yl)methanesulfonamide was treated with 2‐phenyl‐1‐chloroethyne followed by 1‐chloro‐1‐hexadecyne. After these reactions, Pd‐catalyzed double C−H cyclization was employed to produce 1H‐2‐phenyl‐7‐tetradecylbenzofuro[7,6‐g]indole. Notably, this compound transformed into a fan‐shaped structure at 86 °C and transitioned into a smectic A phase characterized by a layered structure.

Funder

Asahi Glass Foundation

Iwatani Naoji Foundation

Tokuyama Science Foundation

Research Foundation for the Electrotechnology of Chubu

Takahashi Industrial and Economic Research Foundation

Tokyo Institute of Technology

Publisher

Wiley

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