Multicomponent reactions (MCRs) facilitate the rapid and diverse construction of molecular scaffolds with modularity and step economy. In this work, engagement of boronic acids as carbon nucleophiles culminates in a Passerini-type three-component coupling reaction towards the synthesis of an expanded inventory of α-hydroxyketones with skeletal diversity. In addition to the appealing features of MCRs, this protocol portrays good functional group tolerance, broad substrate scope under mild conditions and operational simplicity. The utility of this chemistry is further demonstrated by amenable modifications of bioactive products and pharmaceuticals as well as in the functionalization of products to useful compounds.

Reported herein is as tereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids.T his strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions.Incomparison with the conventional approaches,each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Zisomer of aryl alkylk etoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Zisomer of aryl alkylo ximes,aclass of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides,a nd amides having as ingle configuration.

A new chiral Brønsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2‐aryl‐substituted N‐unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3‐protonation and hydride‐transfer processes. Besides, bulky C2‐alkyl‐substituted N‐unprotected indoles are also suitable for this system.

Organoboron compounds play an important role in various fields due to the diversified transformations of C-B bonds. Introduction of easy-to-transform functional groups into organoboron compounds would greatly increase its synthetic...

A novel synthesis of halogenated gem-diboronates (X-CR(Bpin)2) was developed. The reagents are stable and easy to prepare in a large scale. Tetra-substituted halogenated gem-diboronates can be prepared in high yields when using alkylsubstituted gem-dihalides, providing a new strategy for the synthesis of new gem-diboron compounds.