Base-promoted domino-borylation-protodeboronation strategy

Abstract

Abundant multi-borylated compounds, such as alkyl 1,2-bis(boronates), gem-diborylalkanes and 1,1,2-tris(boronates) are constructed via the base-promoted DBP strategies, which can undergo selective protodeboronation, giving many borylated molecules.

C-F bond activation under transition-metal-free conditions

“…In 2016, Hosoya's group [91] reported a single C-F bond cleavage of trifluoromethylarenes with an ortho-silyl group (Scheme 32). The activation of the hydrosilyl group with a trityl cation in the presence of nucleophiles allowed for selective C-F bond functionalization (183)(184)(185)(186)(187)(188)(189). The authors proposed that the reaction was triggered by hydride abstraction or underwent a concerted pathway involving hydride abstraction and C-F bond cleavage.…”

“…Organoborane compounds are ubiquitous in various organic transformations, which are significant synthetic inter-mediates for the construction of pharmaceuticals, natural products, and organic materials [185][186][187][188]. Therefore, the development of simple and convenient methods for the assembly of organoborane compounds has received intensive attention [188].…”

“…Organoborane compounds are ubiquitous in various organic transformations, which are significant synthetic inter-mediates for the construction of pharmaceuticals, natural products, and organic materials [185][186][187][188]. Therefore, the development of simple and convenient methods for the assembly of organoborane compounds has received intensive attention [188]. Among them, direct borylation of nonactivated aromatic hydrocarbon compounds has become the subject of a wealth of landmark studies over the past several decades, as it represents a straightforward conversion from inert raw materials to value-added chemical building blocks.…”

“…Among them, direct borylation of nonactivated aromatic hydrocarbon compounds has become the subject of a wealth of landmark studies over the past several decades, as it represents a straightforward conversion from inert raw materials to value-added chemical building blocks. A battery of transition metals has been dominantly employed as a catalyst for defluorinative borylation of arenes [188]. Despite the transition-metal-catalyzed borylations, transition-metal-free borylation reactions have attracted ongoing interest.…”

Organosuperbase Catalyzed 1,1-Diboration of Alkynes

“…Organoboron compounds are unarguably one of the most valuable families of synthetic building blocks in organic chemistry. [1][2][3][4][5] Multiboronate precursors have recently attracted immense attention from synthetic chemists due to their versatile and tunable reactivity, especially in the cross-coupling chemistry that leads to a plethora of organic structures, bioactive compounds and advanced functional materials. 6,7 Diborylalkenes are probably the most utilized synthetic precursors in this sub-class, as they offer distinctive pathways to the construction of multi-substituted alkenes in regio-or stereoselective manner.…”