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Sandmeyer‐Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by Copper 下载免费PDF全文
Christian Matheis Victoria Wagner Prof. Dr. Lukas J. Goossen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(1):79-82
Aromatic and heteroaromatic diazonium salts were efficiently converted into the corresponding trifluoromethylthio‐ or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. These Sandmeyer‐type reactions proceed within one hour at room temperature, are applicable to a wide range of functionalized molecules, and can optionally be combined with the diazotizations into one‐pot protocols. 相似文献
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Synthesis of Aryl Tri‐ and Difluoromethyl Thioethers via a CH‐Thiocyanation/Fluoroalkylation Cascade 下载免费PDF全文
Dr. Kévin Jouvin Christian Matheis Prof. Dr. Lukas J. Goossen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(41):14324-14327
An AlCl3‐catalyzed C?H thiocyanation was discovered and combined with a Langlois‐type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N‐thiocyanatosuccinimide (NTS) and Ruppert–Prakash reagent. An analogous combination with a copper‐mediated difluoromethylation gives access to aryl difluoromethyl thioethers. Both processes proceed with exceptional regioselectivity for the most electron‐rich, sterically least hindered position of the arene. The sulfur and fluoroalkyl groups originate from different sources, so that the use of expensive, preformed fluoroalkylthiolation reagents is avoided. 相似文献
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Trifluoromethylthiolation and Trifluoromethylselenolation of α‐Diazo Esters Catalyzed by Copper 下载免费PDF全文
Christian Matheis Prof. Dr. Lukas J. Goossen 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(35):12270-12273
α‐Diazo esters are smoothly converted into the corresponding trifluoromethyl thio‐ or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. This straightforward method gives high yields under neutral conditions at room temperature and is applicable to a wide range of functionalized molecules, including diverse α‐amino acid derivatives. It is well‐suited for the late‐stage introduction of trifluoromethylthio or ‐seleno groups into drug‐like molecules. 相似文献
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