A Detailed Study of Irradiation Requirements Towards an Efficient Photochemical Wohl-Ziegler Procedure in Flow

被引：32

作者：

Bonfield, Holly E. ^{[1
]}

Williams, Jason D. ^{[1
,2
]}

Ooi, Wei Xiang ^{[1
]}

Leach, Stuart G. ^{[1
]}

Kerr, William J. ^{[2
]}

Edwards, Lee J. ^{[1
]}

机构：

[1] GlaxoSmithKline Med Res Ctr, API Chem, Gunnels Wood Rd, Stevenage SG1 2NY, Herts, England

[2] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

来源：

CHEMPHOTOCHEM | 2018年 / 2卷 / 10期

关键词：

flow chemistry; halogenation; microreactors; photochemistry; reaction mechanisms; PHOTOREDOX CATALYSIS; SYNTHETIC APPLICATIONS; BENZYLIC BROMINATIONS; N-BROMOSUCCINIMIDE; ONE-POT; LIGHT; OPTIMIZATION; PRECURSORS; INHIBITORS; OXIDATION;

D O I：

10.1002/cptc.201800082

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A platform has been developed to enable standardization of light sources, allowing consistent scale-up from high-throughput screening in batch to flow, using the same pseudo-monochromatic light source. The impact of wavelength and light intensity on a photochemical reaction was evaluated within this platform using the Wohl-Ziegler benzylic bromination of 4-methyl-3-(trifluoromethyl)benzonitrile with N-bromosuccinimide as a model system. It was found that only 40% of the maximum light intensity was required while still maintaining reaction rate, allowing more reliable temperature control and lower energy consumption. The optimized reaction conditions were subsequently applied to a range of synthetically relevant (hetero)aromatic compounds under continuous conditions, exploring the scope of the process within a mild and scalable procedure.

引用

页码：938 / 944

页数：7

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