3047-23-2

Usage

InChI:InChI=1/C10H10Cl2/c1-2-3-4-8-5-6-9(11)10(12)7-8/h2,5-7H,1,3-4H2

Upstream product

• 6287-38-3 3,4-dichlorobenzaldehyde 
• 591-87-7 Allyl acetate 
• 61428-00-0 (3,4-Dichlor-benzyliden)-hydrazin 
• 24850-33-7 allyltributylstanane 
• 18880-04-1 3,4-dichlorobenzyl bromide 

Relevant academic research and scientific papers

Designed electron-deficient gold nanoparticles for a room-temperature Csp3-Csp3coupling reaction

Stille cross-coupling reactions catalysed by an ideal catalyst combining the high activity of homogeneous catalysts and the reusability of heterogeneous catalysts are of great interest for C-C bond formation, which is a widely used reaction in fine chemistry. Despite great effort to increase the utilization ratio of surface metal atoms, the activity of heterogeneous catalysts under mild conditions remains unsatisfactory. Herein, we design a proof-of-concept strategy to trigger the room-temperature activity of heterogeneous Au catalysts by decreasing the electron density at the interface of a rationally designed Schottky heterojunction of Au metals and boron-doped carbons. The electron-deficient Au nanoparticles formed as a result of the rectifying contact with boron-doped carbons facilitate the autocleavage of C-Br bonds for highly efficient C-C coupling reactions of alkylbromides and allylstannanes with a TOF value of 5199 h-1 at room temperature, surpassing that of the state-of-the-art homogeneous catalyst. This journal is

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.