Buchspies Jonathan, Rahman Md Mahbubur, Szostak Roman, Szostak Michal
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
Department of Chemistry, Wroclaw University, F. Joliot-Curie 14, Wroclaw 50-383, Poland.
Org Lett. 2020 Jun 19;22(12):4703-4709. doi: 10.1021/acs.orglett.0c01488. Epub 2020 Jun 1.
The development of new amide precursors for selective, catalytic activation of carbon-nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki-Miyaura cross-coupling of -acylcarbazoles and -acylindoles with arylboronic acids by a highly selective N-C(O) cleavage. The key amide bond ground-state destabilization stems from N to Ar conjugation and enables us for the first time to achieve reactivity similar to that for -acylsulfonamide and -acylcarbamate activation in simple anilides.
开发用于酰胺中碳 - 氮键选择性催化活化的新型酰胺前体是这一新兴反应领域的一个基本目标。我们报道了通过高度选择性的N - C（O）裂解，钯催化的α - 酰基咔唑和α - 酰基吲哚与芳基硼酸的铃木 - 宫浦交叉偶联反应。关键的酰胺键基态去稳定化源于从氮到芳基的共轭作用，这使我们首次在简单的苯胺类化合物中实现了与α - 酰基磺酰胺和α - 酰基氨基甲酸酯活化相似的反应活性。
