Cu(I)-Catalyzed 6-endo-dig Cyclization of Terminal Alkynes, 2-Bromoaryl Ketones, and Amides toward 1-Naphthylamines: Applications and Photophysical Properties

被引：0

作者：

Su, Lebin ^{[1
]}

Ren, Tianbing ^{[1
]}

Dong, Jianyu ^{[1
,2
]}

Liu, Lixin ^{[1
]}

Xie, Shimin ^{[1
]}

Yuan, Lin ^{[1
]}

Zhou, Yongbo ^{[1
]}

Yin, Shuang-Feng ^{[1
]}

机构：

[1] State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha,410082, China

[2] Department of Educational Science, Hunan First Normal University, Changsha,410205, China

来源：

Journal of the American Chemical Society | 2019年 / 141卷 / 06期

关键词：

Functional group substituted 1-naphthylamines; especially N-methylated ones; play important roles in numerous chemical and biological processes. However; these compounds' general and stepeconomic syntheses are highly limited; which seriously restricts efforts to improve the properties and develop new functions for this kind of compound. In this report; we describe the development of an efficient; convenient; and general method for the synthesis of valuable functionalized 1-naphthylamines directly from readily available terminal alkynes; 2-bromoaryl ketones; and amides via Cu(I)-catalyzed benzannulation in a green solvent (i.e; water) under Pd- and ligand-free conditions. A total of 82 functionalized 1-naphthylamines; especially synthetically and biologically useful N-methylated compounds; are synthesized in isolated yields up to 95%. Some unique features of the reaction are as follows: (1) exclusive 6-endo-dig selectivity; (2) ready incorporation of a broad range of functional groups directly from easily available substrates; and (3) amides that can be used as aminating agents and that are excellent alternatives to toxic and/or odorous amines. Due to facile tuning of functional groups for the reaction; the products possess good electronic donor-acceptor structures and exhibit intriguing photophysical properties; such as tunable and polarity-sensitive fluorescence emission and large Stokes shifts (up to 258 nm). Utilizing the products' unique polaritysensitive fluorescence response; we successfully applied the 1-naphthylamine derivatives; such as compound 91; to image lipid droplets (LDs) and monitor cellular LDs growth. The previously mentioned advantages of this methodology; along with the mild conditions; simple operation; and scalable synthesis; may allow this novel reaction to be extended to varied applications in chemistry; biology; and materials science. © 2019 American Chemical Society;

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页码：2535 / 2544