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Synlett

Volumn , Issue 3, 2009, Pages 495-499

Highly efficient and facile aryl transfer to aldehydes using ArB(OH) 2-GaMe3

(5) Jia, Xuefeng a Fang, Ling a Lin, Aijun a Pan, Yi a Zhu, Chengjian a,b

a NANJING UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Aryl transfer; Benzaldehyde; Diarylmethanol; Phenylboronic acid; Trimethylgallium

Indexed keywords

EID: 62249167357 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087552 Document Type: Article

Times cited : (12)

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- General Experimental Procedure The arylboronic acid (0.3 mmol, 1.5 equiv) was dissolved in anhyd toluene (2 mL) in a 20 mL flame-dried Schlenk reaction tube under argon atmosphere. A commercially available 1 M solution of Me3Ga in toluene (0.9 mmol, 4.5 equiv) was added via syringe dropwise, and the resulting mixture was stirred for 2 h at r.t. followed by the addition of aldehyde (0.2 mmol, After completion of the reaction (monitored by TLC, the reaction solution was quenched with H2O (3 mL) and further extracted with EtOAc (3 x 5 mL, The combined organic layer was dried over Na2SO4. Evaporation of the solvent gave the crude product, which was further purified by preparative TLC (PE-EtOAc, 5:1) to give corresponding pure diarylmethanols
- 4. Evaporation of the solvent gave the crude product, which was further purified by preparative TLC (PE-EtOAc, 5:1) to give corresponding pure diarylmethanols.

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- The reactivity of nitro-substituted benzaldehyde is in agreement with the experimental results in references 3c, 4d-f, but 4-nitrobenzaldehyde is not reactive in reference 2a
- The reactivity of nitro-substituted benzaldehyde is in agreement with the experimental results in references 3c, 4d-f, but 4-nitrobenzaldehyde is not reactive in reference 2a.

41
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- In reference 8g,h, the mechanism of the boron-to-zinc transmetalation has been clarified by theoretical calculations and experimental study. In this process, the mixed zinc species (ArZnEt) is formed
- In reference 8g,h, the mechanism of the boron-to-zinc transmetalation has been clarified by theoretical calculations and experimental study. In this process, the mixed zinc species (ArZnEt) is formed.

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