- Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions
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We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.
- Deng, Xingwang,Zhou, Guan,Tian, Jing,Srinivasan, Rajavel
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p. 7024 - 7029
(2020/12/29)
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- Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
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Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanes via tandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms. This journal is
- Kurouchi, Hiroaki
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supporting information
p. 8313 - 8316
(2020/08/17)
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- Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
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The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.
- Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin
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supporting information
p. 6283 - 6287
(2020/09/02)
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- Amide bond synthesis via silver(I) N-heterocyclic carbene-catalyzed and tert-butyl hydroperoxide-mediated oxidative coupling of alcohols with amines under base free conditions
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We present a base free method for amide bond construction via oxidative coupling of alcohols with amines catalyzed by Silver(I) N-heterocyclic carbenes (Ag(I)-NHCs) and mediated by tert-butyl hydroperoxide (TBHP) in ethanol. The results of controlled experiments suggest that the oxidative coupling proceeds through the formation of aldehyde, then subsequent attack by amine to give hemiaminal, which can then be oxidized to amide.
- Balaboina, Ramesh,Thirukovela, Narasimha Swamy,Vadde, Ravinder,Vasam, Chandra Sekhar
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supporting information
p. 847 - 851
(2019/02/20)
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- An efficient, eco-friendly and sustainable tandem oxidative amidation of alcohols with amines catalyzed by heteropolyanion-based ionic liquids via a bifunctional catalysis process
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An efficient, eco-friendly and sustainable method for the tandem oxidative amidation of alcohols with amines has been reported. Using heteropolyanion-based ionic liquids as the catalyst and tert-butyl hydroperoxide as the oxidant, this amidation reaction is operationally straightforward and provides a series of primary, secondary and tertiary amides derivatives in moderate to good yields. Solvent-free media, microwave-promoted conditions and reusability of catalysts are the main highlights. Further, the proposed bifunctional catalysis mechanistic pathway has been briefly investigated in this report.
- Fu, Renzhong,Yang, Yang,Feng, Wei,Ge, Qiuxia,Feng, Yan,Zeng, Xiaojun,Chai, Wen,Yi, Jun,Yuan, Rongxin
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p. 8319 - 8326
(2016/12/02)
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- Direct oxidative amidation of aldehydes with amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions via a dual-catalysis process
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A simple and efficient procedure for the synthesis of amides directly from aldehydes and amines catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media, and operational simplicity are the main highlights. The proposed dual-catalysis mechanistic pathway was briefly investigated. Furthermore, the heteropolyanion-based ionic liquids were easily reusable for this oxidative amidation.
- Fu, Renzhong,Yang, Yang,Zhang, Jin,Shao, Jintao,Xia, Xuming,Ma, Yunsheng,Yuan, Rongxin
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p. 1784 - 1793
(2016/02/10)
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- CuCl/TBHP catalyzed synthesis of amides from aldehydes and amines in water
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A CuCl/TBHP catalyzed amidation of aldehydes with amine under aqueous media is described. Both aliphatic and aromatic aldehydes coupled with a variety of amines under the reaction conditions employed.
- Lu, Shao-Yi,Badsara, Satpal Singh,Wu, Yi-Chun,Reddy, Daggula Mallikarjuna,Lee, Chin-Fa
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supporting information
p. 633 - 636
(2016/01/26)
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- Transformation of Contact-Explosives Primary Amines and Iodine(III) into a Successful Chemical Reaction under Solvent-Free Ball Milling Conditions
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Any synthetic transformation using contact-explosives primary amines and hypervalent iodine(III) (phenyliodine diacetate) in constrained media (extreme conditions) is practically impossible. Herein, we report a method of controlling the explosion into a successful chemical reaction using the acid-salt NaHSO4. As a proof-of-concept, we considered mechanochemical (ball-milling) cross dehydrogenative coupling (CDC) reaction for the amidation of aldehydes via C-H activation. An isothermal titration calorimetric (ITC) study was helpful to understand the enthalpy changes during the reactions before and after addition of NaHSO4.
- Kumarachar, Tapas,Mal, Prasenjit
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p. 3977 - 3985
(2016/01/25)
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- High throughput 'catch-and-release' synthesis within spatially discrete gel arrays
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A tetrafluorophenol acrylamide monomer unit was synthesised, co-polymerised and grafted onto a glass slide to form individual gel spots. As a proof of principle study, a small library of amides was rapidly synthesised within these gel spots using 'catch-and-release' chemistry, including the biologically interesting quorum sensing acyl-homoserine lactones. The tetrafluorophenol acrylamide gel provides an efficient platform to synthesise and screen small molecules for biological activity.
- Boehner, Christine M.,Marsden, David M.,Sore, Hannah F.,Norton, David,Spring, David R.
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supporting information; experimental part
p. 5930 - 5932
(2010/11/21)
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- Pyrazolopyrimidines as therapeutic agents
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The present invention is directed to pyrazolopyrimidine derivatives of formula (I) wherein the substituents are defined herein, which are useful as kinase inhibitors and as such are useful for affecting angiogenesis and diseases and conditions associated with angiogenesis.
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- Solid phase synthesis of amides using Mukaiyama's reagent
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A new solid-phase synthetic method using Mukaiyama's reagent under mild conditions is reported to prepare amides in high purity without purification after cleavage from the resins.
- Tao, Bin,Boykin, David W.
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- Pyrazolopyrimidines as therapeutic agents
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The present invention provides compounds of Formula I, including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R2, and R3 are defined as described herein.
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