<i>N</i>‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

Bergström, Maria; Ganji, Suresh; Naidu, Veluru Ramesh; Unelius, C. Rikard

doi:10.1002/ejoc.201700173

Cited by 42 publications

(29 citation statements)

References 37 publications

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“…Several attempts at iodination of the aryl ring in 20 using known methodologies, such as AgSO 4 /iodine, as well as hypervalent iodine salts gave both large amounts of oxidized products and poor regioselectivity . A newly designed method that generated the desired material regioselectively involved use of NIS/TFA, after which N ‐methylation went smoothly under mild reductive amination conditions with paraformaldehyde and catalytic amounts of formic acid to form 21 . Removal of the TIPS group using standard TBAF conditions gave a crude solid 22 , esterification of which (DCC, DMAP) ultimately produced the desired iodinated coupling partner 5 .…”

Section: Resultsmentioning

confidence: 99%

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Slack

Seupel

Aue

et al. 2019

Chemistry A European J

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As tereoselective total synthesis of O,N-dimethylhamatine, an analogueo fa na xially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route featuresalate-stage atropo-diastereoselective biarylb ond formation. Generationo ft his especially challenging, sterically hinderedt etra-ortho-substituted array was achieved by using Nolan's (IPr*NHC)PdCinCl pre-catalyst undermild Negishicoupling conditions. Discussion is offered regarding the selectivity obtained experimentally and predictedf rom DFT calculations on the keyb iaryl coupling step that leads to the desired M-diastereomer. Figure 1. Structures of tetra-ortho-substituted biarylt etrahydroisoquinolines.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Slack

Seupel

Aue

et al. 2019

Chemistry A European J

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“…This enantiomer represents a lower analog of the corresponding bridgehead‐tetramethylated 2‐hydroxy‐TBTQ derivative. [19a] Finally, the iodine functionality was incorporated by reacting the TBTQ‐phenol with N ‐iodosuccinimide (NIS) in a mixture of trifluoroacetic acid (TFA) and acetonitrile at ambient temperature , . Workup furnished the corresponding 2‐hydroxy‐3‐iodo‐4b 1 ‐methyltribenzotriquinacene ( M )‐ 10 in 53 % yield as a further optically pure TBTQ derivative.…”

Section: Resultsmentioning

confidence: 99%

Combining Stereoselective Enzyme Catalysis with Chirality‐Assisted Synthesis in Tribenzotriquinacene Chemistry

et al. 2018

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The stereoselective synthesis of enantiomerically pure single‐wing‐functionalized tribenzotriquinacenes using the enzyme CAL‐B was successfully extended towards operating on a multi‐gram scale. Based on the (P)‐tribenzotriquinacene‐2‐carbaldehyde (P)‐6 obtained in >99 % ee, the hitherto unknown (P)‐2‐hydroxy‐ and (M)‐2‐hydroxy‐3‐iodo‐TBTQ derivatives (P)‐9 and (M)‐10 were prepared in optically pure form. The bowl‐shaped ortho‐iodophenol (M)‐10 was subjected to a twofold crosswise Ullmann‐type condensation to give, albeit in low yield (10 %), the 1,4‐dioxine 5, in which two TBTQ bowls are fused exclusively in a syn‐bi‐concave orientation, thus demonstrating a new example for a chirality‐assisted synthesis. The corresponding Ullmann condensation of the racemic TBTQ‐ortho‐iodophenol rac‐10 furnished the respective anti‐bis‐TBTQ‐dioxine 11 as the major diastereomer together with the syn‐isomer 5 in the same total yield and in a 11/5 ratio of at least 4. The two diastereomeric bis‐TBTQ‐dioxines show minor but significant differences in most of the characteristic 1H‐NMR chemical shifts. The solid‐state structure of the syn‐dimer 5, determined by X‐ray diffraction, was found to consist of pairs of host–guest complexes, [5·CH2Cl2]2, with pronounced face‐to‐face orientation of the bi‐concave host molecules.

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“…bond activation/acyloxylation, [16] our research was initiated by briefly evaluating the substituted pattern of various thoizole directing groups. As indicated in Table 1, direct electrophilic iodination preferred to occurring on the thiazole bearing active site [17] (DG 1 ), which restrained the aimed ortho-iodination. Introducing methyl group to C-5 site of thiazole drastically promoted the reaction both on reaction rate and yield (DG 2 ).…”

Section: Scheme 1 Previous Related Work and Present Workmentioning

confidence: 99%

Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp²)-H Bond Iodination Reaction

Xing¹,

Shao²,

Fu³

et al. 2019

Chinese Journal of Organic Chemistry

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A palladium-catalyzed ortho-C(sp 2)-H bond iodination of 4-arylthiazoles has been developed. Through screening of directing groups and optimazation of reaction parameters, the most efficient reaction conditions for mono-ortho-position iodination were obtained, which were applied to synthesize a series of 4-(2-iodoaryl)thiazoles with broad scope of 4-arylthiazole substrates. Furthermore, the iodine group can be easily transformed into other organic functional groups, which improved the application value of this methodology. At last, plausible mechanism was proposed based on an intermolecular deuterium labeling kinetic experiment and radical inhibition experiments. Keywords palladium-catalyzed; 4-arylthiazoles; mono-selectivity; C(sp 2)-H bond; iodination 2 Results and discussion Given our recent success in thiazole-directed C(sp 2)-H Chinese Journal of Organic Chemistry ARTICLE

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N‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

Cited by 42 publications

References 37 publications

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Combining Stereoselective Enzyme Catalysis with Chirality‐Assisted Synthesis in Tribenzotriquinacene Chemistry

Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp²)-H Bond Iodination Reaction

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N‐Iodosuccinimide (NIS) in Direct Aromatic Iodination

Cited by 42 publications

References 37 publications

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine

Combining Stereoselective Enzyme Catalysis with Chirality‐Assisted Synthesis in Tribenzotriquinacene Chemistry

Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp2)-H Bond Iodination Reaction

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Product

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Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp²)-H Bond Iodination Reaction