Das, Siuli; Mondal, Rakesh; Chakraborty, Gargi; Guin, Amit Kumar; Das, Abhishek; Paul, Nanda D. published an article in 2021. The article was titled 《Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach》, and you may find the article in ACS Catalysis.Synthetic Route of C7H5BrO The information in the text is summarized as follows:
Herein an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-ones I (R = H, 2-Br, 4-Cl, 4-Me, etc.; X = C=O) and 1,2,3,4-tetrahydro-2-phenylquinazolines I (X = CH2) using a Zn(II)-stabilized azo-anion radical complexes II (R1 = H, Cl) as the catalyst was reported. A simple, easy to prepare and bench stable Zn(II)-complex III (R1 = Cl) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction of azo-anion radical species II (R1 = Cl) which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-ones I (X = C=O) and 1,2,3,4-tetrahydro-2-phenylquinazolines I (X = CH2) under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles IV (R2 = n-Bu, Ph, thiophen-2-yl, etc.; R3 = H, Me; R4 = H, Br, Me), V (R5 = H, Cl) and VI (R6 = H, Cl; R7 = H, Me; R8 = Ph, 2-fluorophenyl, pyridin-2-yl, etc.) via dehydrogenative coupling of alcs. R2CH2OH and 2-NH2-4-R6-C6H3CH2OH with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.o-Bromobenzaldehyde(cas: 6630-33-7Synthetic Route of C7H5BrO) was used in this study.
o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Synthetic Route of C7H5BrOSynthetic applications of o-Bromobenzaldehyde include: synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction, preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary