ChemInform Abstract: An Attempt of Preparation of 2,8-Di-tert.-Butyl-10,11-dihydro-5H-dibenzo(a,d)cycloheptene by C-C Coupling Reaction of 4,4′-Di-tert.-Butyl-2,2′-bis(chloromethyl)diphenylmethane.

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

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Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert-Butyl Nitrite

Synlett ◽

10.1055/s-0036-1589038 ◽

2017 ◽

Vol 28 (16) ◽

pp. 2153-2156 ◽

Cited By ~ 13

Author(s):

Wen-Ting Wei ◽

Hongze Liang ◽

Wen-Ming Zhu ◽

Weida Liang ◽

Yi Wu ◽

...

Keyword(s):

Room Temperature ◽

Coupling Reaction ◽

Cross Coupling ◽

Coupling Reactions ◽

Phenol Derivative ◽

Tert Butyl ◽

Radical Coupling ◽

Air Atmosphere ◽

Cross Coupling Reaction ◽

Temperature Water

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.

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Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide

Synlett ◽

10.1055/s-0036-1589106 ◽

2017 ◽

Vol 29 (02) ◽

pp. 215-218 ◽

Cited By ~ 3

Author(s):

Wei-Wei Ying ◽

Wen-Ming Zhu ◽

Hongze Liang ◽

Wen-Ting Wei

Keyword(s):

Coupling Reaction ◽

Metal Catalyst ◽

Butyl Hydroperoxide ◽

Alkyl Radicals ◽

Tert Butyl ◽

Radical Coupling ◽

Tert Butyl Hydroperoxide ◽

Radical Coupling Reaction ◽

Efficient Route ◽

Novel Strategy

A novel strategy has been developed for the synthesis of indoline-2,3-diones through a metal-free radical-coupling reaction. Alkyl radicals derived from indolin-2-ones through a radical-transfer reaction combine with the tert-butylhydroperoxy radical readily generated from commercially available tert-butyl hydroperoxide to afford 3-(tert-butylperoxy)indolin-2-one intermediates that can be further transformed into indoline-2,3-diones under air. This strategy provides a simple and eﬃcient route to the construction of a C=O bond without the use of any metal catalyst or base.

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Synthesis of Perfluoro-tert-butyl Tyrosine, for Application in 19F NMR, via a Diazonium-Coupling Reaction

Organic Letters ◽

10.1021/acs.orglett.6b02858 ◽

2016 ◽

Vol 18 (24) ◽

pp. 6240-6243 ◽

Cited By ~ 14

Author(s):

Caitlin M. Tressler ◽

Neal J. Zondlo

Keyword(s):

Coupling Reaction ◽

19F Nmr ◽

Tert Butyl ◽

Diazonium Coupling

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TBHP/n-Bu4PBr-Promoted Oxidative Cross-Dehydrogenative Coupling of Aryl Methanols: A Facile Synthesis of Symmetrical Carboxylic Anhydride Derivatives

Synlett ◽

10.1055/s-0036-1590905 ◽

2017 ◽

Vol 29 (01) ◽

pp. 136-140

Author(s):

Mehdi Adib ◽

Rahim Pashazadeh

Keyword(s):

Transition Metal ◽

Coupling Reaction ◽

Catalytic Amount ◽

Facile Synthesis ◽

Butyl Hydroperoxide ◽

Metal Free ◽

Tert Butyl ◽

Dehydrogenative Coupling ◽

Tert Butyl Hydroperoxide ◽

Methylene Groups

A transition-metal-free oxidative cross-dehydrogenative coupling reaction has been developed for the preparation of symmetrical carboxylic anhydrides through self-coupling dual C–O bond formations of aryl methanols. In the presence of a catalytic amount of tetrabutylphosphonium bromide (TBPB) as transfer agent and aqueous tert-butyl hydroperoxide (TBHP) as oxidant and reactant, methylene groups of aryl methanols were efficiently oxidized to C=O and coupled with the peroxide oxygen from TBHP to form a diverse array of symmetrical carboxylic anhydride derivatives.

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Synthesis and Structure of (Nitronyl Nitroxide-2-ido)(tert-butyldiphenylphosphine)gold(I) and -(Di(tert-butyl)phenylphosphine)gold(I) Derivatives; Their Comparative Study in the Cross-Coupling Reaction

Crystals ◽

10.3390/cryst10090770 ◽

2020 ◽

Vol 10 (9) ◽

pp. 770

Author(s):

Igor Zayakin ◽

Irina Bagryanskaya ◽

Dmitri Stass ◽

Maxim Kazantsev ◽

Evgeny Tretyakov

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Oxidation Potential ◽

Nitronyl Nitroxide ◽

X Ray ◽

Tert Butyl ◽

Cross Coupling Reaction ◽

Vis Spectroscopy ◽

The Cross ◽

Derivatives Of

We synthesized two new organogold derivatives of a nitronyl nitroxide (NN) with phosphine ligands, namely NN-Au-PtBuPh2 and NN-Au-PtBu2Ph. They were characterized by X-ray diffraction analysis, cyclic voltammetry, and ESR, IR, and UV/Vis spectroscopy. The X-ray structural analysis revealed a tendency of the NN moiety to form a large number of short intermolecular contacts. This phenomenon is related to the anionic nature of the paramagnetic group NN, as evidenced by a significantly lower oxidation potential in comparison with purely organic derivatives of NN radicals. The cross-coupling reaction of NN-Au-PPh3, NN-Au-PtBuPh2, or NN-Au-PtBu2Ph with an activated bromoarene, namely, p-BrC6H4NO2, was investigated. It was shown that regardless of the presence of the bulky tert-butyl substituent, all gold derivatives have similar activities in the cross-coupling reaction and give a cross-coupling product, NN-C6H4NO2, with comparable yields.

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Synthesis of Mono- and Bis-Pyrazoles Bearing Flexible p-Tolyl Ether and Rigid Xanthene Backbones, and Their Potential as Ligands in the Pd-Catalysed Suzuki–Miyaura Cross-Coupling Reaction

Catalysts ◽

10.3390/catal9090718 ◽

2019 ◽

Vol 9 (9) ◽

pp. 718

Author(s):

Zahid Hussain ◽

Cristiane Schwalm ◽

Raoní Rambo ◽

Renieidy Dias ◽

Rafael Stieler ◽

...

Keyword(s):

Catalytic System ◽

Good Yield ◽

Coupling Reaction ◽

Cross Coupling ◽

Boronic Acids ◽

Aryl Halides ◽

Tert Butyl ◽

Cross Coupling Reaction ◽

Ullmann Coupling

The present work describes the synthesis of mono- and bis-pyrazole compounds bearing flexible p-tolyl ether and rigid 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene backbones as pyrazolyl analogues of DPEphos and Xantphos ligands, respectively. The synthesis of new pyrazolyl analogues was accomplished following an Ullmann coupling protocol, and the resulting products were isolated in overall good yields. In addition, a hybrid imidazolyl–pyrazolyl analogue bearing a xanthene backbone was synthesized using the same protocol, whereas a hybrid selanyl–pyrazolyl analogue with a xanthene backbone was synthesized in a good yield employing a second C–H activation step. The symmetrical bis-pyrazolyl and the hybrid imidazolyl–pyrazolyl analogues were found to be the most active among the new ligands evaluated in the Pd-catalysed Suzuki-Miyaura cross-coupling of aryl halides with aryl boronic acids. A simple catalytic system based on Pd(OAc)2/2a was developed, which efficiently catalyses the Suzuki–Miyaura reaction of aryl halides and aryl boronic acids and provides moderate to excellent yields of the corresponding cross-coupling products.

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Facile Total Synthesis of Isopregomisin

Journal of Chemical Research ◽

10.1177/174751989902300246 ◽

1999 ◽

Vol 23 (2) ◽

pp. 158-159

Author(s):

Wang Mingyi ◽

Yang Hongfang ◽

Wu Anxin ◽

Pan Xinfu

Keyword(s):

Total Synthesis ◽

Grignard Reagent ◽

Coupling Reaction ◽

Tert Butyl ◽

Efficient Route

Isopregomisin, a diarylbutane-lignan, has been synthesized by a short and efficient route starting from pyrogallol; the synthesis involves a novel selective demethylation reaction and the coupling reaction of the Grignard reagent produced from an aryl bromopropane with ( E)-2- tert-butyl-3-phenyloxaziridine.

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Medium-size cyclophanes. Part 601: Synthesis and conformational studies of 9-substituted [3.3]metacyclophane-2,11-diones and conversion to the corresponding [3.3]metacyclophanes

Canadian Journal of Chemistry ◽

10.1139/v02-072 ◽

2002 ◽

Vol 80 (5) ◽

pp. 510-516 ◽

Cited By ~ 14

Author(s):

Takehiko Yamato ◽

Koji Tsuchihashi ◽

Noriko Nakamura ◽

Mai Hirahara ◽

Kan Tanaka

Keyword(s):

Charge Transfer ◽

Coupling Reaction ◽

Sodium Hydride ◽

Medium Size ◽

Substituted Benzenes ◽

Conformational Studies ◽

Tert Butyl ◽

Type Interaction

Various syn- and anti-9-substituted [3.3]metacyclophane-2,11-diones are obtained by the coupling reaction of the corresponding 2,6-bis(bromomethyl)benzenes (3) with 2,6-bis[2-cyano-2-(toluenesulfony)ethyl]-4-tert-butyl-1-substituted benzenes (4) in dimethylformamide (DMF) with an excess of sodium hydride. Depending on the substituents at positions 1 and 4 on 3, different yields (inversion of selectivity) of anti-5 and syn-5 were achieved.Key words: metacyclophanes, cyclization, conformation, CH-π interaction, through-space interaction, charge-transfer-type interaction.

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