Benzylation of Arenes with Benzyl Halides under Promoter‐Free and Additive‐Free Conditions

Cheng, Xinqiang; Jiang, Shan; Tian, Xiaochen; Ren, Yunlai; Zhu, Yanyan

doi:10.1002/ejoc.201900590

Cited by 9 publications

(9 citation statements)

References 117 publications

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“…This compound is known. 30 1,3,5-Trimethyl-2-(4-methylbenzyl)benzene (3b). Colorless oil, yield 91% (122.5 mg); 73% (98.3 mg); Eluent: Petroleum ether/ EtOAc = 40/1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound is known. 30 2-(4-Chlorobenzyl)-1,3,5-trimethylbenzene (3h). White solid, yield 80% (117.5 mg); 75% (110.1 mg); Eluent: Petroleum ether/ EtOAc = 40/1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound is known. 30 2-(4-Bromobenzyl)-1,3,5-trimethylbenzene (3i 13 C{ 1 H} NMR (125 MHz CDCl 3 ): δ 167.2, 145.9, 137.0, 136.1, 132.9, 129.7, 129.0, 127.9, 127.8, 52.0, 34.9, 20.9, 20.1. GC-MS (EI, 70 eV) m/z = 268 (M + ).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H₃PO₃/I₂

Xiao

Xiang

et al. 2021

J. Org. Chem.

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For the first time, H 3 PO 3 was used as both the reducing reagent and the promotor in the reductive benzylation reactions with aryl aldehydes. By using a H 3 PO 3 /I 2 combination, various aromatic aldehydes underwent iodination reactions and Friedel−Crafts type reactions with arenes via benzyl iodide intermediates, readily producing benzyl iodides and diarylmethanes in good yields. Intramolecular cyclization reactions also took place, giving the corresponding cyclic compounds. This new strategy features easy-handling, low-cost, and metal-free conditions.

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“…This compound is known. 30 1,3,5-Trimethyl-2-(4-methylbenzyl)benzene (3b). Colorless oil, yield 91% (122.5 mg); 73% (98.3 mg); Eluent: Petroleum ether/ EtOAc = 40/1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound is known. 30 2-(4-Chlorobenzyl)-1,3,5-trimethylbenzene (3h). White solid, yield 80% (117.5 mg); 75% (110.1 mg); Eluent: Petroleum ether/ EtOAc = 40/1.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 1 more Smart Citation

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H₃PO₃/I₂

Xiao

Xiang

et al. 2021

J. Org. Chem.

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“…13 C NMR (125 MHz, CDCl 3, ppm): δ= 137.0 135.6, 135.1, 134.0, 129.1, 128.9, 127.8, 34.3, 21.0, 20.9, 20.1 Elemental analysis calcd (%) for (C 17 H 20 ) ( 3 c ): 91.01, H 8.99. found: C 90.96, H 8.99. This is a known compound [28] …”

Section: Methodsmentioning

confidence: 99%

“…Elemental analysis calcd (%) for (C 16 H 18 ) ( 3 e ): C 91.37, H 8.63 found: C 91.12, H 8.64. This is a known compound [28] …”

Section: Methodsmentioning

confidence: 99%

Temperature‐Assisted Generation of Arylmethyl Radicals from Bis(arylmethyl)tin Dichlorides: Efficient Reagents for − Bond‐Forming Reactions

Dhanwant

Saini

Chivers

et al. 2023

Chemistry A European J

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The oxidative-addition reaction between an arylmethyl chloride (RCH 2 Cl; R=1-C 10 H 7 , 2,4,6-Me 3 C 6 H 2 , 4-MeC 6 H 4 , 3-MeC 6 H 4 , C 6 H 5 , 4-ClC 6 H 4 ) and tin powder in boiling toluene produces bis(arylmethyl)tin dichlorides, [(RCH 2 ) 2 SnCl 2 ] in good yields. At 160 °C in mesitylene bis(1-naphthylmethyl)tin dichloride undergoes SnÀ C homolytic cleavage to generate two 1-naphthylmethyl radicals (1-C 10 H 7 CH 2 * ) which were trapped by TEMPO (C 9 H 8 NO * ). Subsequently, the radicals (RCH 2 * ) produced in this manner were utilized for efficient substitution reactions with electron-rich arenes (R'H; R' = 2,4,6-Me 3 C 6 H 2 , 1,2,4,5-Me 4 C 6 H, 1,2,3,4,5-Me 5 C 6 ) to obtain a variety of unsymmetrical diarylmethanes (RR'CH 2 ). The addition of one equivalent of iodine (I 2 ) to the reaction mixture resulted in a significant increase in the yields of coupled products.

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