Regioselective Construction of Functionalized Biarylols by Fe(OTf)₃‐Catalyzed Direct Arylation of 1‐Diazonaphthalen‐2(1H)‐ones and Their Fluorescence Properties

Abstract

A facile and efficient protocol for the construction of functionalized biarylols by Fe(OTf)3‐catalyzed direct arylation of 1‐diazonaphthalen‐2(1H)‐ones with arenes has been developed. This methodology provides diverse 1‐arylnaphthalen‐2‐ols in moderate to good yields. This approach has also been applied to the synthesis of biologically interesting polycyclic‐aromatic‐substituted and heteroaryl‐substituted naphthalen‐2‐ols. The synthesized compounds bearing an anthracene scaffold can be useful as potential fluorescent biomarkers for confocal imaging of clone cells.

Diazo Quinone: An Effective Phenolic Precursor for Building C(sp2)−C(sp2) Bonds

“…Since molecules with a 2-naphthol moiety have shown important biological and pharmacological properties, [39] this protocol provides access to various novel and valuable 3naphthyl-indoles (43) in high yields (up to 94 % yield). In addition, the direct coupling of benzofuran, pyrrole, and furan with 6 afforded the corresponding 2-or 3-naphthyl substituted heterocycles (44)(45)(46) in good yields and high regioselectivity (Scheme 9). [40] Alternatively, starting from oalkynylphenols (47) in the presence of a gold catalyst, Sun and co-workers were able to obtain furan derivatives (48) or furan-gold intermediates (49).…”

“…In 2017, Lee and co-workers described a novel protocol for the direct arylation of 1-diazonaphthalen-2(1H)-ones ( 6) with sterically hindered electron-rich arenes catalyzed by Fe(OTf) 3 , and a variety of 1-arylnaphthalen-2-ols (63-64) were obtained in moderate to good yields (Scheme 11). [44] This method was applied to the synthesis of biologically interesting polycyclic-aromatic-substituted naphthalen-2-ols (65)(66), where these compounds with anthracene scaffolds can used as potential fluorescent biomarkers for confocal imaging of clone cells.…”

Bismuth(III)-Catalyzed Oxidative Cross-Coupling of 3-Hydroxycarbazoles with Arenols under an Oxygen Atmosphere

“…The oxidative cross-coupling (OCC) of two aromatic compounds is a powerful and useful tool for C–C bond formation and the synthesis of various C 1 -symmetric biaryls. − Particularly, the OCCs of carbazoles have attracted considerable attention because of the wide versatility of the products in the pharmaceutical and materials science fields. − Recently, several vanadium-catalyzed chemo- and regioselective OCCs of carbazoles were reported (Scheme A). − Although transition-metal catalysts are extremely efficient for biaryl synthesis, their toxicity can be a drawback. This problem can be overcome using heterogeneous catalysts; , however, certain limitations, such as metal-catalyst leaching, still remain.…”

Borane-Catalyzed Carbazolation Reactions of Aryldiazoacetates

“…The challenge in the development of such a transformation lies within the control of the regioselectivity, as either N–H or C–H functionalization can occur. The successful development, however, would overcome the need for precious metal catalysts in such transformations and showcase important advances in the area of Lewis acid-mediated reactions of diazoalkanes. It would consequently aid in the understanding of the reactivity pattern and application of this concept in organic synthesis.…”