Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions

• 来源期刊: 中国科学:化学（英文版）
• 年，卷（期）: 2020,（3）
• 页码范围: 370-376
• 页数: 7页
• 语种: 英文

摘要

N-Acylpyrrole-type amides are a class of versatile building blocks in asymmetric synthesis.We report that by employing Ni(COD)2/2,2'-bipyridine (5 mol％) catalytic system,the direct,catalytic alcoholysis of N-acylpyrrole-type aromatic and aliphatic amides with both primary and secondary alcohols can be achieved efficiently under very mild conditions (rt,1 h) even at gram scale.By increasing the catalyst loading to 10 mol％,prolonging reaction time (18 h),and/or elevating reaction temperature to 50 ℃/80 ℃,the reaction could be extended to both complex and hindered N-acylpyrroles as well as to N-acylpyrazoles,N-acylindoles,and to other (functionalized) primary and secondary alcohols,In all cases,only 1.5 equiv.of alcohol were used.The value of the method has been demonstrated by the racemization-free,catalytic alcoholysis of chiral amides yielded from other asymmetric methodologies.