Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization

Mandapati, Usharani; Pinapati, Srinivasarao; Tamminana, Ramana; Rudraraju, Rameshraju

doi:10.1007/s10562-017-2234-y

Cited by 8 publications

(2 citation statements)

References 76 publications

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“…More recently, arylisothiocyanates 1358 were regioselectively halogenated by means of copper catalysis (Scheme 780). 1927 Here, stoichiometric copper(II) halides served a dual role, namely as halogen source and as the promotor. The reaction proceeded at ambient reaction temperature to furnish the halogenated arylisothiocyanates 1359 in good yields and mono-selectivity.…”

Section: Scheme 505 Pincer Nickel(ii)-catalyzed C−h Bond Alkylation O...mentioning

confidence: 99%

3d Transition Metals for C–H Activation

et al. 2018

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C−H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material sciences, crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these C−H functionalizations required precious 4d or 5d transition metal catalysts. Given the cost-effective and sustainable nature of earth-abundant first row transition metals, the development of less toxic, inexpensive 3d metal catalysts for C−H activation has gained considerable recent momentum as a significantly more environmentally-benign and economically-attractive alternative. Herein, we provide a comprehensive overview on first row transition metal catalysts for C−H activation until summer 2018.

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Section: Scheme 505 Pincer Nickel(ii)-catalyzed C−h Bond Alkylation O...mentioning

confidence: 99%

3d Transition Metals for C–H Activation

et al. 2018

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“…Various isothiocyanante arenes were ortho-halogenated in high yields (Scheme 46). [175] Later on, in 2018, Mandapati and co-workers used iodobenzene diacetate and copper(I) halides for the ortho-halogenation of 2-arylpyridines (Scheme 47). [176] Notably, the copper(I) halides acted as the halogen source alongside the catalyst since no external halogen sources were required for the conversion.…”

Section: Directed Cà H Halogenation Reactions Of C(sp 2 )à H Bonds Of...mentioning

confidence: 99%

Recent Advances in First‐Row Transition‐Metal‐Mediated C−H Halogenation of (Hetero)arenes and Alkanes

et al. 2022

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The ubiquity of carbon halogen bonds in the structural core of numerous biomolecules and pharmaceuticals along with their role as synthetic precursors in various organic reactions makes the organic halides a crucial class of organic compounds. Consequently, the synthesis of organic halides with high regioselectivity is of paramount importance in synthetic chemistry. In nature, selective halogenation is achieved by metalloenzymes with high efficiency involving high-valent iron-oxo as active species. The high selectivity of halogenating enzymes attracted considerable attention leading to the development of several biomimetic approaches for CÀ H halogenation. Moreover, the emergence of transition metal (TM) catalyzed site-selective CÀ H halogenation protocols through the development of several directed strategies has also been impressive. There has been significant development in the first row TM catalyzed CÀ H halogenation reactions despite the dominance of late transition metals catalysts in this field. But in literature, there is no up-to-date recent review article that consolidates bio-mimetic as well as synthetic strategies of CÀ H halogenation (X = Cl, Br, I) containing organo-fluorination with all the first-row transition metals. Thus, we got motivated and have focused to elucidate the recent developments of first row TM-catalyzed CÀ H halogenation of (hetero)arenes and alkanes through biomimetic approaches as well as directed and undirected strategies in this present review. Additionally, this review covers the recent progresses in the CÀ H fluorination methodologies. Altogether, the review will provide a combined overview of all the strategies of first-row transition-metalmediated CÀ H halogenation reactions that may benefit the scientific community towards the development of new methodologies in this field.

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Copper‐Catalyzed sp ² CH Bond Functionalization

Jain

Kaur

Sharma

2022

Handbook of CH-Functionalization

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The use of sp 2 CH bonds as key functional groups has been realized by transition metal‐mediated CH bond activation and functionalization. In this regard, copper‐catalyzed CH activation has emerged as an environmentally benign and economically attractive approach in modern synthetic organic chemistry. Copper salts serve as versatile catalysts for oxidative coupling reactions and are often proposed to serve as a one‐electron oxidant to promote the single‐electron transfer process. This article discusses the recent advances in the copper‐catalyzed sp 2 CH functionalization achieving CC, CN, CO, CS, and CX bond formation via direct CH activation as well as directing group‐assisted activation strategy. An understanding of the mechanism of these reactions involving organocopper intermediates is crucial to promote the discovery of efficient and highly selective catalytic systems.

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Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization

Cited by 8 publications

References 76 publications

3d Transition Metals for C–H Activation

3d Transition Metals for C–H Activation

Recent Advances in First‐Row Transition‐Metal‐Mediated C−H Halogenation of (Hetero)arenes and Alkanes

Copper‐Catalyzed sp ² CH Bond Functionalization

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Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C–H Functionalization

Cited by 8 publications

References 76 publications

3d Transition Metals for C–H Activation

3d Transition Metals for C–H Activation

Recent Advances in First‐Row Transition‐Metal‐Mediated C−H Halogenation of (Hetero)arenes and Alkanes

Copper‐Catalyzed sp 2 CH Bond Functionalization

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Copper‐Catalyzed sp ² CH Bond Functionalization