- Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights
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We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).
- Kurouchi, Hiroaki,Sai, Masahiro
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supporting information
p. 3585 - 3591
(2021/06/27)
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- Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2
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The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed. A range of acrylamides and arylboronic acids were compatible with this reaction under redox-neutral conditions, leading to a series of malonate derivatives that are versatile building blocks in organic syntheses.
- Cai, Lei,Fu, Lei,Gao, Yuzhen,Li, Gang,Li, Shangda,Zhou, Chunlin
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supporting information
p. 7328 - 7332
(2020/11/19)
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- NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives
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A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.
- Wu, Lingang,Hao, Yanan,Liu, Yuxiu,Wang, Qingmin
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p. 6762 - 6770
(2019/07/22)
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- UV light-mediated difunctionalization of alkenes through aroyl radical addition/1,4-/1,2-Aryl shift cascade reactions
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UV light-mediated difunctionalization of alkenes through an aroyl radical addition/1,4-/1,2-aryl shift has been described. The resulted aroyl radical from a photocleavage reaction added to acrylamide compounds followed by cyclization led to the formation of oxindoles, whereas the addition to cinnamic amides aroused a unique 1,4-aryl shift reaction. Furthermore, the difunctionalization of alkenes of prop-2-en-1-ols was also achieved through aroyl radical addition and a sequential 1,2-aryl shift cascade reaction.
- Zheng, Lewei,Huang, Hongli,Yang, Chao,Xia, Wujiong
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p. 1034 - 1037
(2015/03/30)
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- SYNTHESIS OF FUNCTIONALIZED AND UNFUNCTIONALIZED OLEFINS VIA CROSS AND RING-CLOSING METATHESIS
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The invention is directed to the cross-metathesis and ring-closing metathesis reactions between geminal disubstituted olefins and terminal olefins, wherein the reaction employs a Ruthenium or Osmium metal carbene complex. Specifically, the invention relates to the synthesis of alpha-functionalized or unfunctionalized olefins via intermolecular cross-metathesis and intramolecular ring-closing metathesis using a ruthenium alkylidene complex. The catalysts preferably used in the invention are of the general formulawherein:M is ruthenium or osmium;X and Xare each independently an anionic ligand;L is a neutral electron donor ligand; and,R, RR, R, R, and Rare each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.
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Paragraph 0018; 0024
(2015/11/09)
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- Palladium-catalyzed [3+3] annulation between diarylamines and α,β-unsaturated acids through C-H activation: Direct access to 4-substituted 2-quinolinones
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A C-H activation strategy has been successfully employed for the high-yielding synthesis of a diverse array of 4-substituted 2-quinolinone species by a palladium-catalyzed dehydrogenative coupling involving diarylamines. This intermolecular annulation app
- Kancherla, Rajesh,Naveen, Togati,Maiti, Debabrata
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supporting information
p. 8360 - 8364
(2015/06/02)
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- Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation
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A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.
- Ueda, Satoshi,Okada, Takahiro,Nagasawa, Hideko
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supporting information; experimental part
p. 2462 - 2464
(2010/08/13)
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- Synthesis and pharmacological evaluation of newer substituted benzoxazepine derivatives as potent anticonvulsant agents
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A series of 2-substitutedphenyl-3-(substitutedphenylamino)methyl-2,3- dihydro-4-diphenylamino-1,5-benzoxazepines (4a-4p) and 2-substitutedphenyl-3- substitutedphenylazo-2,3-dihydro-4-diphenylamino-1,5-benzoxazepines (5a-5p) have been synthesized from 2-substitutedphenyl-2,3-dihydro-4-diphenylamino-1,5- benzoxazepines (3a-3d) by the Mannich reaction and diazotization reaction, respectively. All these compounds were screened, in vivo, for their anticonvulsant activity and acute toxicity studies. Compounds 4p and 5p were found to be most potent compounds of this series and were compared with the reference drug phenytion sodium, lamotrigine and sodium valproate. The structures of these compounds have been established by IR, 1H NMR and mass spectroscopic data.
- Bajaj, Kiran,Archana,Kumar, Ashok
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p. 369 - 376
(2007/10/03)
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- Palladium(II)-catalyzed regioselective carbonylative coupling of aniline derivatives with terminal aryl acetylenes to give acrylamides under syngas conditions
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The carbonylative coupling of aniline derivatives (1a-h) with terminal aryl acetylenes (2a, b) catalyzed by Pd(OAc)2 and 1,4- bis(diphenylphosphino)butane (dppb) under syngas conditions affords acrylamide derivatives 3 or 3' in excellent yields
- El Ali,El-Ghanam,Fettouhi,Tijani
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p. 5761 - 5764
(2007/10/03)
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