Photochemical and electrochemical C–N borylation of arylhydrazines

Du, Linlin; Sun, Li; Zhang, Hua

doi:10.1039/d1cc06145c

Cited by 16 publications

(13 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The transition metal‐free C−N borylation of arylhydrazine hydrochlorides with B 2 pin 2 was reported by our group employing photochemical and electrochemical conditions (Scheme 20). [45] In general, photochemical borylation exhibits higher efficiency than electrochemical borylation, which might be attributed to the dehydrazination side reaction in the electrochemical process. As arylhydrazine hydrochlorides are stable and easily available, the prompt synthesis of aryl boronate esters could be achieved by employing this protocol.…”

Section: Aromatic C−n Borylationmentioning

confidence: 99%

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Luo

Tang

et al. 2023

The Chemical Record

Self Cite

View full text Add to dashboard Cite

Aromatic organoboron compounds are highly valuable building blocks in organic chemistry. They were mainly synthesized through aromatic C−H and C−Het borylation, in which transition metal‐catalysis dominate. In the past decade, with increasing attention to sustainable chemistry, numerous transition metal‐free C−H and C−Het borylation transformations have been developed and emerged as efficient methods towards the synthesis of aromatic organoboron compounds. This account mainly focuses on recent advances in transition metal‐free aromatic C−H, C−N, C−S, and C−O borylation transformations and provides insights to where further developments are required.

show abstract

Section: Aromatic C−n Borylationmentioning

confidence: 99%

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Luo

Tang

et al. 2023

The Chemical Record

Self Cite

View full text Add to dashboard Cite

show abstract

“…19 In 2022, Zhang and co-workers reported the C-N borylation of arylhydrazine hydrochlorides with B 2 pin 2 as the borylating reagent by employing electrochemical conditions (Scheme 7a). 20 A variety of aryl boronate esters could be accessed promptly from bench stable and easily available arylhydrazines via this scalable transition metal-free electrochemical transformation. Very recently, the same group achieved the electrochemical borylation of nitroarenes to prepare aryl boronic esters in moderate to good yields with good functional group tolerance (Scheme 7b).…”

Section: C-n Borylationmentioning

confidence: 99%

Electrochemical synthesis and transformation of organoboron compounds

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…Hua Zhang et al discovered that the diboron reagents are electrochemically compatible, which could lead to new electrochemical borylation processes (Scheme 17). [78] Bis(pinacolato)diboron was used to CÀ N borylate arylhydrazine hydrochlorides under photochemical and electrochemical conditions. This novel and scalable transformation provides a transition-metal-free synthesis route to aryl boronate esters from arylhydrazines.…”

Section: Electrochemical C-n Borylationmentioning

confidence: 99%

Progress in the Electrochemical Synthesis of Organoboron Compounds

Moniruzzaman

Afrin

Ali³

2023

Asian J Org Chem

View full text Add to dashboard Cite

Organoboron is a class of compounds widely used in organic synthesis, pharmaceuticals, material science, sensors, and so on. Therefore, the development of efficient and selective electrochemical methods to synthesize organoboron has attracted much interest as an emerging sustainable technique of organic synthesis. Here, we summarized research on electrochemical borylations, including the electrochemically driven borylation of arenes, alkanes, aryl, or alkyl halides, activated carboxylic acids etc., based on direct electrolysis and metal‐free organocatalysis. We focus on the reaction mechanisms involved in single‐electron transfer and other radical processes. We believe that this review will inspire electrochemists to discover more efficient transformations to expand this field of borylation.

show abstract

Photochemical and electrochemical C–N borylation of arylhydrazines

Abstract: The C–N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synthetic routes towards...

Cited by 16 publications

References 33 publications

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

Electrochemical synthesis and transformation of organoboron compounds

Progress in the Electrochemical Synthesis of Organoboron Compounds

Contact Info

Product

Resources

About