55230-18-7Relevant academic research and scientific papers
Late-Stage Intermolecular Allylic C-H Amination
Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina
supporting information, p. 14969 - 14975 (2021/10/01)
Allylic amination enables late-stage functionalization of natural products where allylic C-H bonds are abundant and introduction of nitrogen may alter biological profiles. Despite advances, intermolecular allylic amination remains a challenging problem due to reactivity and selectivity issues that often mandate excess substrate, furnish product mixtures, and render important classes of olefins (for example, functionalized cyclic) not viable substrates. Here we report that a sustainable manganese perchlorophthalocyanine catalyst, [MnIII(ClPc)], achieves selective, preparative intermolecular allylic C-H amination of 32 cyclic and linear compounds, including ones housing basic amines and competing sites for allylic, ethereal, and benzylic amination. Mechanistic studies support that the high selectivity of [MnIII(ClPc)] may be attributed to its electrophilic, bulky nature and stepwise amination mechanism. Late-stage amination is demonstrated on five distinct classes of natural products, generally with >20:1 site-, regio-, and diastereoselectivity.
Copper-catalyzed oxidative esterification of ortho-formyl phenols without affecting labile formyl group
Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang
supporting information, p. 4569 - 4573 (2015/07/02)
A copper-catalyzed oxidative esterification of ortho-formyl phenols with aldehydes using TBHP as oxidant in water is developed. Besides aromatic and aliphatic aldehydes, benzylic alcohols are also suitable for this reaction. The sensitive formyl group rem
Synthesis of 3-substituted coumarins from 2-(acyloxy)arylaldehydes using the TiCl4/R3N reagent system
Suresh, Surisetti,Periasamy, Mariappan
, p. 688 - 690 (2007/10/03)
3-Substituted coumarins are formed in 37-63% yields by the reaction of 2-(acyloxy)arylaldehydes with the TiC4/R3N reagent system. The structure of the compound 2c was determined by single crystal X-ray analysis.
