Pd-Catalyzed Stereoselective 1,2-Aryboration of Alkenylarenes

Abstract

The palladium-catalyzed highly regio- and diastereoselective arylboration of alkenylarenes has been developed. This chemistry afforded the benzylic boronic esters with a broad substrate scope, which are valuable synthetic intermediates for organic synthesis. The chiral anion phase-transfer strategy was designed for this transformation to realize the regio-, diastereo-, and enantioselective control of this reaction simultaneously.

Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Bromides and Chlorosilanes

“…Despite the above breakthroughs, innovations for the cross-coupling of normal alkyl electrophiles and chlorosilanes are still needed due to the great utility of alkyl silanes. Our research interest focused on the selective construction of the C–B and C–Si bonds . Herein we developed a nickel-catalyzed reductive cross-coupling of alkyl bromide and chlorosilane to construct a primary C­(sp 3 )–Si bond with good functional group tolerance (Scheme B-3).…”

Copper‐Catalyzed Highly Selective Protoboration of CF3‐Containing 1,3‐Dienes

“…Based on our previous research, [10] this study was commenced with the copper-catalyzed reaction of CF 3 -containing 1,3-dienes 1a,L iO t Bu, B 2 Pin 2 and EtOH. Interestingly,w ith PPh 3 as ligand, the above reaction afforded the desired product 2a with 21 %yield (Entry 1, Table 1).…”

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

“…In addition to Heck-type C–C bond formations, arylboration of alkenes with aryl diazonium salts was also reported. − In 2015, an enantioselective Pd-catalyzed arylboration of α-olefins, using aryl diazonium salts, and bis­(pinacolato)­diboron 134 was disclosed, allowing the direct preparation of enantioenriched benzylic boronates 135 (Scheme ). Mechanistically, upon interaction with the lipophilic chiral phosphoric acid anion, the insoluble aryl diazonium salt undergoes phase transfer to provide a soluble chiral ion pair 136 .…”