132680-49-0

Upstream product

• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 108-95-2 phenol 
• 85630-23-5 N,N-diethyl-O-(2-trimethylsilylphenyl)carbamate 

Downstream Products

• 628339-19-5 N,N-diethyl-1-carbamoyloxy-2-chloro-6-methylsulfanylbenzene 
• 1025324-59-7 2-but-2-ynoyl-6-chlorophenyl diethylcarbamate 
• 95-57-8 2-monochlorophenol 
• 850036-50-9 N,N-diethyl-2-hydroxy-3-chlorobenzamide 
• 1445899-15-9 2-chloro-6-hydroxyphenyl diethylcarbamate 
• 681123-07-9 2-(3-chloro-2-hydroxy-phenylsulfanyl)-N,N-diethyl-acetamide 

Relevant academic research and scientific papers

Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation

The directed ortho-lithiation reactions of O-aryl N,N-dialkylcarbamates as well as O-1-naphthyl and O-2-naphthyl N,N-dialkylcarbamates with sec-butyllithium/tetramethylethylenediamine (sBuLi/TMEDA) followed by quenching with various electrophiles afford a range of polysubstituted aromatic compounds. If the solutions of the ortho-lithiated carbamates are warmed to room temperature without the addition of external electrophiles, salicylamide and 1- and 2-hydroxynaphthamide derivatives are formed through anionic ortho-Fries rearrangements. The relative stabilities and reactivities of different O-aryl N,N-dialkylcarbamates were investigated. The lateral metalation of 2-tolyl carbamates with lithium diisopropylamide (LDA) provides a route to benzo[b]furan-2(3H)-ones. Previously reported results are used in a comparison of seven O-based directed metalation groups in reactions with several electrophiles. The described methodology is useful for the preparation of 1,2,3-substituted aromatic compounds.

Directed ortho metalation-based methodology. Halo-, nitroso-, and boro-induced ipso-desilylation. Link to an in situ Suzuki reaction

(Chemical Equation Presented) Treatment of DoM-derived silylated aromatics 2-4 under standard electrophilic halogenation conditions cleanly affords ipso-desilyation products 5-7, while nitration of methoxy-substituted analogues 8, 9 leads to non-ipso isomers 10, 12 and 11, 13, controlled by a silicon steric effect. Sequential ipso-borodesilylation of 2a, 3a, and 20 followed by treatment with aryl halides under Pd-catalyzed conditions constitutes an in situ Suzuki-Miyaura cross-coupling protocol to biaryls and heterobiaryls 23.