Synlett 2017; 28(16): 2147-2152
DOI: 10.1055/s-0036-1588182
letter
© Georg Thieme Verlag Stuttgart · New York

Rhodium(III)-Catalyzed Sequential Cleavage of Two C–H Bonds for the Synthesis of Polyarylated Naphthols

Ruokun Feng
b  Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Department of Chemistry, Shaoxing University, Shaoxing 312000, P. R. of China
,
Yuan Gao
b  Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Department of Chemistry, Shaoxing University, Shaoxing 312000, P. R. of China
,
Zhanxiang Liu*
a  Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou 310027, P. R. of China   Email: [email protected]   Email: [email protected]
,
Yuhong Zhang*
a  Department of Chemistry, ZJU-NHU United R&D Center, Zhejiang University, Hangzhou 310027, P. R. of China   Email: [email protected]   Email: [email protected]
c  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author Affiliations
Funding from the Science Technology Department of Zhejiang Province (No. LQ15B020002) and NSFC (Nos. 21472165 and 21672186) is gratefully acknowledged.
Further Information

Publication History

Received: 14 May 2017

Accepted after revision: 16 May 2017

Publication Date:
04 July 2017 (online)


Abstract

A Rh(III)-catalyzed multiple C–H bond activation/cyclization of phenol derivatives with alkynes was developed. Polyaryl-substituted naphthol derivatives, potentially useful as organic optoelectronic materials, were obtained in moderate to good yields.

Supporting Information

 
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  • 14 Polyarylaryl Dimethylcarbamates 4; General Procedure A 25 mL sealed tube equipped with a magnetic stirrer bar was charged with [Cp*RhCl2]2 (3 mg, 0.005 mmol), AgSbF6 (7 mg, 0.02 mmol), Cu(OAc)2 (80 mg, 0.4 mol), carbamate 1 (0.2 mmol), alkyne 2 (0.5 mmol), and PhF (2.0 mL). The tube was then sealed and heated at 110 °C with stirring for 12 h. After cooling, the mixture was filtered through a plug of Celite, which was then washed with EtOAc (3 × 20 mL). The combined organic phases were washed with brine (2 × 20 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, EtOAc–PE). 1,2,3,4-Tetraphenyl-9-anthryl Dimethylcarbamate (4aa) Yellow solid; yield: 86 mg (76%); mp 227–229 °C. IR (KBr): 1727, 1160 cm–1. 1H NMR (400 MHz, CDCl3, TMS): δ = 2.47 (s, 3 H), 2.71 (s, 3 H), 6.67–6.69 (m, 1 H), 6.77–6.84 (m, 9 H), 7.00–7.03 (m, 1 H), 7.07–7.11 (m, 1 H), 7.15–7.17 (m, 2 H), 7.23 (m, 2 H), 7.27–7.43 (m, 6 H), 7.77–7.80 (m, 2 H), 8.12 (s, 1 H). 13C NMR (100 MHz, CDCl3, TMS): δ = 36.1, 36.4, 121.4, 123.7, 124.7, 125.0, 125.3, 125.5 (2C), 125.8, 126.2, 126.4, 126.6, 127.6, 127.7, 128.6, 129.8, 131.1, 131.2, 131.4, 131.7, 132.1, 134.8, 138.4, 138.6, 139.9, 140.4, 140.6, 141.1, 142.5, 143.5, 154.2. HRMS (EI): m/z [M+] calcd for C41H31NO2: 569.2355; found: 569.2358.