Hui-Liang Hua

Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes

A novel and highly practical reaction for the copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes is presented here. This methodology provides a general and straightforward way to synthesize a variety of useful CF3-containing nitriles, which can be used for further preparation of pharmaceutically and agrochemically important compounds in synthetic organic chemistry.

Copper-catalyzed three-component cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes.

A novel three-component strategy for the cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid and concise access to addition-carbocyclization products. Furthermore, the products obtained can be useful building blocks in discoveries of lead compounds and other biologically active CF3-containing heterocycles.

AgSCF3-Mediated Trifluoromethylthiolation/Radical Cascade Cyclization of 1,6-Enynes

A AgSCF3-mediated radical cascade cyclization/trifluoromethylthiolation of 1,6-enynes triggered by a C-C triple bond is developed. This protocol also provides another opportunity to construct a valuable trifluoromethylthio-substituted polycyclic fluorene system through the formations of one C-SCF3 bond and two C-C bonds in a single step.

Convenient and Highly Efficient Routes to 2 H‐Chromene and 4‐Chromanone Derivatives: Iodine‐Promoted and p‐Toluenesulfonic Acid Catalyzed Cascade Cyclizations of Propynols

A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99 %). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.

Palladium-catalyzed arene C–H activation/ketone C–H functionalization reaction: route to spirodihydroindenones

A novel palladium and norbornene catalyzed arene C–H activation method to synthesize various spirodihydroindenone derivatives was developed. This method produces spirodihydroindenones employing aryl iodides with 2-(2-bromoethyl)-cyclopentanones via a domino reaction, which simplifies the route of building spiro compounds and expands further applications for functional groups selectivity.

CCDC 1486021: Experimental Crystal Structure Determination

Related Article: Yi-Feng Qiu, Xin-Yu Zhu, Ying-Xiu Li, Yu-Tao He, Fang Yang, Jia Wang, Hui-Liang Hua, Lan Zheng, Li-Chen Wang, Xue-Yuan Liu, and Yong-Min Liang|2015|Org.Lett.|17|3694|doi:10.1021/acs.orglett.5b01657