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钯催化三氟甲磺酸钠与芳基（杂芳基）三氟甲磺酸酯反应合成芳基和杂芳基三氟甲磺酰化合物

Pd-Catalyzed Synthesis of Aryl and Heteroaryl Triflones from Reactions of Sodium Triflinate with Aryl (Heteroaryl) Triflates.

作者信息

Smyth Lynette A, Phillips Eric M, Chan Vincent S, Napolitano José G, Henry Rodger, Shekhar Shashank

机构信息

AbbVie Inc., Deutschland GmbH & Co. KG, Knollstraße, 67061 Ludwigshafen, Germany.

AbbVie Inc., Process Research and Development, 1 North Waukegan Road, North Chicago, Illinois 60064, United States.

出版信息

J Org Chem. 2016 Feb 5;81(3):1285-94. doi: 10.1021/acs.joc.5b02523. Epub 2016 Jan 21.

DOI:10.1021/acs.joc.5b02523
PMID:26735925
Abstract

A novel method for Pd-catalyzed triflination of aryl and heteroaryl triflates using NaSO2CF3 as the nucleophile is described. The combination of Pd2(dba)3 and RockPhos formed the most effective catalyst. A broad range of functional groups and heteroaromatic compounds were tolerated under the neutral reaction conditions. The order of reactivity ArOTf ≥ ArCl ≥ ArBr is consistent with transmetalation being a slow step of the reaction.

摘要

描述了一种使用NaSO2CF3作为亲核试剂，钯催化芳基和杂芳基三氟甲磺酸酯进行三氟甲基化的新方法。Pd2(dba)3和RockPhos的组合形成了最有效的催化剂。在中性反应条件下，多种官能团和杂芳族化合物均可耐受。反应活性顺序ArOTf≥ArCl≥ArBr与转金属化是反应的慢步骤一致。

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