76041-87-7

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 109-89-7 diethylamine 
• 62924-92-9 N,N-diethyl-2-(trimethylsilyl)benzamide 
• 1696-17-9 N,N-diethylbenzamide 
• 88-67-5 2-Iodobenzoic acid 

Downstream Products

• 1696-17-9 N,N-diethylbenzamide 
• 1312885-66-7 5-[2-(diethylcarbamoyl)phenyl]-2-ethoxy-2-methylbenzo[d][1,3]dioxol-4-yl diethylcarbamate 
• 38063-26-2 5-hydroxybenzophenanthrene 
• 1413417-14-7 N,N-diethyl-2-(phenylethynyl)benzamide 
• 1551274-41-9 (E)-N-ethyl-N-(3-(iodo(phenyl)methylene)benzo[c]thiophen-1(3H)-ylidene)ethanaminium iodide 
• 123251-49-0 bis[2-(N,N-diethylaminocarbonyl)phenyl] diselenide 

Relevant academic research and scientific papers

Lipshutz-type bis(amido)argentates for directed: Ortho argentation

Bis(amido)argentate (TMP)2Ag(CN)Li2 (3, TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics- A nd transition metal-susceptible substituents such as methyl ester, aldehyde, vinyl, iodo, (trifluoromethanesulfonyl)oxy and nitro groups. The arylargentates displayed good reactivity with various electrophiles. Chalcogen (S, Se, and Te) installation and azo coupling reactions also proceeded efficiently.

Synthesis of Phenacene-Helicene Hybrids by Directed Remote Metalation

Polycyclic aromatic hydrocarbons (PAHs) with six and seven rings were synthesized via directed metalation and cross-coupling of chrysenyl N,N-diethyl carboxamides with o-tolyl and methylnaphthalenyl derivatives. In the presence of competing ortho sites, the site selectivity in iodination of chrysenyl amides by directed ortho metalation (DoM) was influenced by the lithium base. The catalyst ligand bite angle was presumably important in the cross-coupling of sterically hindered bulky PAHs. Subsequent directed remote metalation of biaryls under standard conditions and at elevated temperatures afforded various fused six- and seven-ring PAHs, all in good yields and with fluorescent properties.

Reactions of Hexadehydro-Diels-Alder (HDDA)-Derived Benzynes with Thioamides: Synthesis of Dihydrobenzothiazino-Heterocyclics

Reaction of thioamides (e.g., II) with benzynes generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization (e.g., I) produces dihydrobenzothiazines (e.g., III). It is postulated that the reaction proceeds via benzothietene (cf. IV) and o-thiolatoa

KOtBu-mediated synthesis of dimethylisoindolin-1-ones and dimethyl-5-phenylisoindolin-1-ones: Selective C-C coupling of an unreactive tertiary sp3 C-H bond

A new reaction for the synthesis of dimethylisoindolinones has been presented from 2-halo-N-isopropyl-N-alkylbenzamide substrates and KO tBu by the selective C-C coupling of an unreactive tertiary sp 3 C-H bond. The reaction manifest

Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine

Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the cor

Formation of benzo[c]thiophen-1-aminium iodide by the reaction of o-alkynylbenzothioamide with iodine

Reaction of o-alkynylbenzothioamide with molecular iodine was investigated. Unique benzo[c]thiophen-1-aminium iodide was obtained when the tertiary thioamide was used as a reactant. The reaction proceeded efficiently in less polar solvent, whereas the cor

Concerning the structures of alkali-metal-mediated ortho zincation of benzamides and phenyl O -carbamate

As a further contribution to alkali-metal-mediated metalation, a method for converting C-H bonds directly to C-Zn bonds without the need for an additional salt metathesis step, reactions of the sodium TMP-zincate [(TMEDA)Na(μ-TMP) (μ-tBu)Zn(su

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.

Deprotonative cadmation of functionalized aromatics

This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases. The Royal Society of Chemistry.

Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines

Palladium-catalyzed cross-couplings represent a powerful method for the formation of new bonds. A catalytic, enantioselective P-C bond-forming reaction proceeding via a Pd-mediated arylation of silylphosphines was developed for the synthesis of P-stereoge