Direct Intramolecular Aminoboration of Allenes
Chunhua Yang, Meng Han, Wenyan Li, Ningning Zhu, Zhenzhen Sun, Junjie Wang, Zhantao Yang, Yue‐Ming Li
Abstract
Direct intramolecular aminoboration of sulfonamidoallenes was realized using BCl3 as a boron source. The reactions benefited from the interaction between BCl3 and sulfonamides and provided a variety of borylvinyl heterocycles in good isolated yields. When chiral substrates were involved in the reactions, high stereoselectivity was observed, as can be ascertained by single-crystal X-ray diffraction experiments. Derivatization of the thus-obtained borylvinyl compounds proceeded readily, and different functionalities could be obtained via oxidation, halogenation, and Suzuki coupling reactions.
Topics & Concepts
Intramolecular forceChemistryHalogenationDerivatizationStereoselectivityBoronCombinatorial chemistrySingle crystalOrganic chemistryStereochemistryCatalysisCrystallographyHigh-performance liquid chromatographyOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques