Cross Dehydrogenative Coupling (CDC) Reactions of N,N‐Disubstituted Formamides, Benzaldehydes and Cycloalkanes

Abstract

Abstract:In recent years, reactions of inexpensive and easily available formamides, benzaldehydes and cycloalkanes with various coupling partners have made an impact in the field of cross dehydrogenative coupling. Even in the absence of a benzylic C-H site or a heteroatom at the α-position, these sub-

Recent Advances in Visible-Light-Induced Cross Dehydrogenation Coupling Reaction under Transition Metal-Free Conditions

“…1.1 C(sp 3 )-C(sp 3 )偶联 2011 年, Tan 课题组 [34] 报道了可见光诱导叔胺的 α- 同年, König 等 [35] 以 Eosin Y 染料作光敏剂, 研究了 可 见 光 诱 导 下 N-芳 基 四 氢 异 喹 啉 和 亲 核 试 剂 的 C(sp 3 )-H/C(sp 3 )-H 偶联反应(Eqs. 3,4). 与前者相比, 该体系具有催化剂用量低, 反应时间短等优点.…”

“…随后, 该课题组[99] 在 Rh-6G 染料和硫酸的催化体系 中实现了甘氨酸酯与 α-当归内酯的交叉脱氢-环化反应 (Scheme 17). 首先甘氨酸酯与 α-当归内酯发生 C(sp3 )-C(sp 2 )偶联反应生成中间体 179b, 随后经过分子内亲核 取代和去质子化得到目标产物 183. 该反应条件温和, 合成的 γ-内酰胺可作为重要中间体合成复杂天然产物.…”

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

“…From the perspectives of new chemistry development, green chemistry, and sustainable procedures, CDC has emerged as remarkable methodology for the synthesis of complex molecules. Transition‐metal (TM)‐catalyzed CDC is the most common reaction; however, it suffers from various drawbacks, such as expensive TM catalysts, and challenges associated with the separation of metal residues from the final products. Thus, TM‐free CDC reactions have attracted prominent attention in recent times, as they avoid expensive TM catalysts and the challenges involved in the removal of toxic metal residues from the desired products.…”

Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents

“…In 2009, one of us reviewed the different roles of DMF, highlighting that DMF is much more than a solvent [ 1 ]. Subsequently, this topic has been documented by the teams of Jiao [ 2 ] and Sing [ 3 ]. For of a book devoted to solvents as reagents in organic synthesis, we wrote a chapter summarizing the reactions consuming DMF and DMAc as carbon, hydrogen, nitrogen and/or oxygen sources [ 4 ].…”