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

共 65 条

[1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].

Allen, Laura J. ;

Cabrera, Pablo J. ;

Lee, Melissa ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610

[2]

Amara Z, 2015, NAT CHEM, V7, P489, DOI [10.1038/NCHEM.2261, 10.1038/nchem.2261]

[3] Carbon tetrachloride free benzylic brominations of methyl aryl halides [J].

Amijs, CHM ;

van Klink, GPM ;

van Koten, G .

GREEN CHEMISTRY, 2003, 5 (04) :470-474

[4] Green Chemistry: Principles and Practice [J].

Anastas, Paul ;

Eghbali, Nicolas .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312

[5]

[Anonymous], 1970, NATL STANDARD REFERE

[6]

[Anonymous], ANGEW CHEM

[7]

[Anonymous], 2012, ANGEW CHEM

[8] Multidrug resistance regulators (MDRs) as scaffolds for the design of artificial metalloenzymes [J].

Bersellini, Manuela ;

Roelfes, Gerard .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (14) :3069-3073

[9] Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment [J].

Cambie, Dario ;

Bottecchia, Cecilia ;

Straathof, Natan J. W. ;

Hessel, Volker ;

Noel, Timothy .

CHEMICAL REVIEWS, 2016, 116 (17) :10276-10341

[10] A Scalable Procedure for Light-Induced Benzylic Brominations in Continuous Flow [J].

Cantillo, David ;

de Frutos, Oscar ;

Rincon, Juan A. ;

Mateos, Carlos ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) :223-229

← 1 2 3 4 5 6 7 →