Copper-boryl mediated organic synthesis

Abstract

Organoboron compounds are valuable synthetic intermediates that find application in a diverse variety of processes including both C-X and C-C bond-forming transformations. This has been achieved by using a variety of boron derivatives. Of these, boronate esters are probably the most versatile and, reflecting this, methods for the generation of boronate esters are of considerable current interest. Given the mild reaction conditions, good functional group tolerance, and low cost of the metal catalyst, the use of copper-boryl reagents is particularly attractive. In this review, methodologies in copper-boryl chemistry are discussed and the many different transformations possible are surveyed.

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

“…[1a-c] Arylboration of alkenes as an important class of such transformations has been developed to prepare alkyl boron compounds. [2] Great advances have been achieved in alkene 1,2-arylborations [3] with an elegant dual metal cooperative catalysis [4] reported by Semba and Nakao and Brown (Figure 1a,l eft). [5,6] However,u nactivated terminal alkenes are still challenging targets in 1,2-arylboration reactions.I n recent years,e fforts have also been devoted to the investigation of alkene arylborations involving metal migration, [7] but only limited examples on 1,1-arylborations by palladium migration have been reported to date (Figure 1a,r ight).…”

Migratory Arylboration of Unactivated Alkenes Enabled by Nickel Catalysis

“…[1] Tr ansition-metal catalysis enables alkene difunctionalization that proceeds in ah ighly selective and efficient manner. [2] Great advances have been achieved in alkene 1,2-arylborations [3] with an elegant dual metal cooperative catalysis [4] reported by Semba and Nakao and Brown (Figure 1a,l eft). [2] Great advances have been achieved in alkene 1,2-arylborations [3] with an elegant dual metal cooperative catalysis [4] reported by Semba and Nakao and Brown (Figure 1a,l eft).…”

Copper‐Catalyzed Cross‐Coupling of Benzylic Bromides with Arylboronic Acids: Synthesis of Diarylalkanes and Preliminary Antifungal Evaluation Against Magnaporthe Grisea

“…[9,10] Copper has showed special reactivity in the cross coupling between alkyl electrophilic reagents and boronates. [11] Fu has devised a clever and the first copper-catalyzed coupling of benzyl halides with arylboronates using diketone family ligand. [12] Very recently, Lee group realized such cross coupling by the dual copper-and photoredox catalysis.…”