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  • Title: Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols.
    Author: Pennamuthiriyan A, Rengan R.
    Journal: J Org Chem; 2024 Feb 16; 89(4):2494-2504. PubMed ID: 38326039.
    Abstract:
    We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols and 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied by elemental and spectroscopic (FT-IR, NMR, and HRMS) analyses. The solid-state molecular structure of complex 2 has been authenticated by a single-crystal X-ray diffraction study. Furthermore, a series of 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide derivatives have been synthesized (24 examples) utilizing a 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling of benzyl alcohols with benzenesulfonamide. Gratifyingly, the catalytic protocol is highly selective with the yield up to 93% and produces eco-friendly water/hydrogen gas as byproducts. The control experiments and plausible mechanistic investigations indicate that the coupling of the in situ generated aldehyde with benzenesulfonamide leads to the desired product. In addition, a large-scale synthesis of one of the thiadiazine derivatives unveils the synthetic usefulness of the current methodology.
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