α-Diazo Ketones in On-Surface Chemistry,Journal of the American Chemical Society

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α-Diazo Ketones in On-Surface Chemistry
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-04-08 , DOI: 10.1021/jacs.8b02599
Lacheng Liu _{1,

2} , Henning Klaasen , Alexander Timmer _{1,

2} , Hong-Ying Gao _{1,

2} , Dennis Barton ₃ , Harry Mönig _{1,

2} , Johannes Neugebauer , Harald Fuchs _{1,

2} , Armido Studer

Affiliation

Polymerization of a biphenyl bis α-diazo ketone on Cu(111) and Au(111) surfaces to provide furandiyl bridged poly-para-phenylenes is reported. Polymerization on Cu(111) occurs via initial N2 fragmentation leading to Cu-biscarbene complexes at room temperature as polymeric organometallic structure. At 135 °C, carbene coupling affords polymeric α,β-unsaturated 1,4-diketones, while analogous alkene formation on the Au(111) surface occurs at room temperature. Further temperature increase leads to deoxygenative cyclization of the 1,4-diketone moieties to provide alternating furandiyl biphenyl copolymers on Cu(111) (165 °C) and Au(111) (240 °C) surfaces. This work shows a new approach to generate Cu-biscarbene intermediates on surfaces, opening the pathway for the controlled generation of biphenyl copolymers.

中文翻译：

表面化学中的α-重氮酮

据报道，联苯双 α-重氮酮在 Cu(111) 和 Au(111) 表面聚合以提供呋喃二基桥联聚对亚苯基。Cu(111) 上的聚合通过初始 N2 碎片发生，导致在室温下作为聚合有机金属结构的 Cu-双碳烯配合物。在 135 °C 时，卡宾偶联产生聚合的 α,β-不饱和 1,4-二酮，而在室温下在 Au(111) 表面上形成类似的烯烃。进一步的温度升高导致 1,4-二酮部分的脱氧环化，从而在 Cu(111) (165 °C) 和 Au(111) (240 °C) 表面上提供交替的呋喃二联苯共聚物。这项工作展示了一种在表面生成 Cu-双碳烯中间体的新方法，为控制生成联苯共聚物开辟了道路。

更新日期：2018-04-08

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