Yangyang Wang

Bio: Yangyang Wang is an academic researcher from East China University of Science and Technology. The author has contributed to research in topics: Borylation & Aryl. The author has an hindex of 1, co-authored 4 publications receiving 5 citations.

Metal-Free ortho-Selective C-H Borylation of 2-Phenylthiopyridines Using BBr3.

Abstract: A novel route for ortho-selective C-H borylation of 2-phenylthiopyridines using BBr3 as the boron source under metal-free conditions has been reported. The reaction exhibited site exclusivity, and the synthesized aryl boronates were freely converted to various useful intermediates. Thus, this facile method would be beneficial to synthesize structurally diversified phenylthioethers derivatives and other materials containing boron-nitrogen coordination.

Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group.

Abstract: The direct arylation of aliphatic ketones has been developed via Pd-catalyzed β-C(sp3)-H bond functionalization with 2-(aminooxy)-N,N-dimethylacetamide as a novel transient directing group (TDG), which showed remarkable directing ability to generate arylated products in moderate to good yields. Furthermore, the reaction can tolerate abundant substrate of ketones and aryl iodides. This study expands the scope of applications for TDGs.

Transient Imine as a Directing Group for the Metal-Free o-C-H Borylation of Benzaldehydes.

Abstract: Organoboron reagents are important synthetic intermediates and have wide applications in synthetic organic chemistry. The selective borylation strategies that are currently in use largely rely on t...

Transient Directing Groups in Metal-Organic Cooperative Catalysis.

Abstract: The direct functionalization of C-H bonds is among the most fundamental chemical transformations in organic synthesis. However, when the innate reactivity of the substrate cannot be utilized for the functionalization of a given single C-H bond, this selective C-H bond functionalization mostly relies on the use of directing groups that allow bringing the catalyst in close proximity to the C-H bond to be activated and these directing groups need to be installed before and cleaved after the transformation, which involves two additional undesired synthetic operations. These additional steps dramatically reduce the overall impact and the attractiveness of C-H bond functionalization techniques since classical approaches based on substrate pre-functionalization are sometimes still more straightforward and appealing. During the past decade, a different approach involving both the in situ installation and removal of the directing group, which can then often be used in a catalytic manner, has emerged: the transient directing group strategy. In addition to its innovative character, this strategy has brought C-H bond functionalization to an unprecedented level of usefulness and has enabled the development of remarkably efficient processes for the direct and selective introduction of functional groups onto both aromatic and aliphatic substrates. The processes unlocked by the development of these transient directing groups will be comprehensively overviewed in this review article.

Pyrimidine-directed metal-free C-H borylation of 2-pyrimidylanilines: a useful process for tetra-coordinated triarylborane synthesis.

Abstract: Convenient, easily handled, laboratory friendly, robust approaches to afford synthetically important organoboron compounds are currently of great interest to researchers. Among the various available strategies, a metal-free approach would be overwhelmingly accepted, since the target boron compounds can be prepared in a metal-free state. We herein present a detailed study of the metal-free directed ortho-C–H borylation of 2-pyrimidylaniline derivatives. The approach allowed us to synthesize various boronates, which are synthetically important compounds and various four-coordinated triarylborane derivatives, which could be useful in materials science as well as Lewis-acid catalysts. This metal-free directed C–H borylation reaction proceeds smoothly without any interference by external impurities, such as inorganic salts, reactive functionalities, heterocycles and even transition metal precursors, which further enhance its importance.

Regio-Selective Transition-Metal-Free C(sp2)-H Borylation: A Subject of Practical and Ongoing Interest in Synthetic Organic Chemistry.

Abstract: Considerable advances have been made in the area of C-H functionalization in the last few decades. A number of approaches including both directed or non-directed strategies have been developed thus far. Among the various C-H functionalizations, C-H borylation is of special interest due to the wide applications of organoborons. In this regard, various transition-metal-catalyzed regio-selective strategies have been appeared. However, the major concern regarding metal-catalyzed C-H borylation protocols is the requirement of a precious metal as well as the contamination of metal precursor in the desired products, which limit the application of this process in large-scale synthesis. Therefore, the recent trends have involved the use of transition-metal-free systems. We summarize this recent ongoing interest of transition-metal-free regio-selective C-H borylation. We believe that this review will definitely help to increase interest in this field and it will stimulate further progress.

Metal-Free ortho-Selective C-H Borylation of 2-Phenylthiopyridines Using BBr3.

Abstract: A novel route for ortho-selective C-H borylation of 2-phenylthiopyridines using BBr3 as the boron source under metal-free conditions has been reported. The reaction exhibited site exclusivity, and the synthesized aryl boronates were freely converted to various useful intermediates. Thus, this facile method would be beneficial to synthesize structurally diversified phenylthioethers derivatives and other materials containing boron-nitrogen coordination.