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Synlett 2017; 28(20): 2936-2940
DOI: 10.1055/s-0036-1588563
DOI: 10.1055/s-0036-1588563
letter
Synthesis of Tetraarylmethanes by the Triflic Acid-Promoted Formal Cross-Dehydrogenative Coupling of Triarylmethanes with Arenes
This work was supported by KAKENHI from JSPS (26810056 and 17K17805 to M.N.). M.N. thanks the Chugai Pharmaceutical Company Award in Synthetic Organic Chemistry, Japan. J.C.-H.Y. is a recipient of a JSPS postdoctoral fellowship for research in Japan (16F16749). We also thank JSPS and NU for funding this research through The World Premier International Research Center Initiative (WPI) programFurther Information
Publication History
Received: 15 June 2017
Accepted after revision: 19 July 2017
Publication Date:
26 September 2017 (online)
Dedicated to Professor Victor Snieckus, colleague, mentor, and friend on the occasion of his 80th birthday.
Abstract
The formal cross-dehydrogenative coupling of triarylmethanes with arenes promoted by triflic acid and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is described. This method provides a variety of tetraarylmethane derivatives in good to excellent yields from triarylmethanes that can be readily prepared by our previous methods. Control experiments suggest a possible catalytic cycle involving the generation of a trityl cation intermediate followed by nucleophilic addition of the arene.
Key words
cross-coupling - dehydrogenation - tetraarylmethanes - triarylmethanes - arylation - organocatalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588563.
- Supporting Information
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References and Notes
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- 18 1-Methoxy-4-tritylbenzene (3aa); Typical Procedure A 10-mL sealable reaction tube equipped with a magnetic stirring bar and a septum was evacuated, flame-dried under vacuum, cooled to r.t., and backfilled with argon. The tube was then charged with Ph3CH (1a; 24.4 mg, 0.1 mmol) and DDQ (45.4 mg, 0.2 mmol, 2 equiv) under a constant stream of argon. The tub was evacuated for 5 min and refilled with argon. This cycle was repeated twice more. DCE (0.3 mL), TfOH (0.9 μL, 0.01 mmol, 10 mol%), and anisole 2a (51 μL, 0.5 mmol, 5 equiv) were added, and the vessel was sealed. The mixture was stirred at 100 °C for 6 h then cooled to r.t. EtOAc (~5 mL) was added, and the solution was passed through a pad of Celite with copious washings with EtOAc. The solvent was evaporated under reduced pressure to give a crude product that was purified by preparative TLC (hexane–EtOAc, 50:1) to give a white solid; yield: 25.9 mg (74%). 1H NMR (400 MHz, CDCl3): δ = 3.78 (s, 3 H), 6.80 (dm, J = 9.2 Hz, 2 H), 6.80 (dm, J = 9.2 Hz, 2 H), 7.16–7.26 (m, 15 H). 13C NMR (150 MHz, CDCl3): δ = 55.2, 64.3, 112.7, 125.8, 127.4, 131.1, 132.2, 139.0, 147.0, 157.5. HRMS (DART): m/z calcd for C26H22O: 350.1671; found: 350.1663.
For reviews, see:
For selected examples, see:
For recent advances for the synthesis of polyarylated alkanes by transition-metal catalysis, see:
For reviews, see:
For examples of reactions of trityl cation with arenes, see:
For recent examples of cross-dehydrogenative coupling using DDQ, see:
In the reaction of 1i with 2g, we did not observe the formation of the corresponding triarylmethanol; however, the p-quinone methide 6 (Figure [2]) was detected by GC/MS. The formation of such p-quinone methides from p-methoxy-substituted triarylmethanol derivatives under acidic conditions through O-demethylation has been reported, see:
This fluorene-formation process might be similar to a Nazrov cyclization: