- Synthesis of diaryl ketones through oxidative cleavage of the C-C double bonds in N -Sulfonyl enamides
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An oxidative cleavage of a C-C double bond is developed from the photochemical [2+2]-cycloaddition of diaryl N-tosyl enamides, aryl heteroaryl N-tosyl enamides, and N-tosyl cyclic enamides with singlet molecular oxygen, followed by a ring-opening reaction mediated by Cs2CO3 under air and sunlight without the use of photosesitizer, producing symmetrical and unsymmetrical diaryl, heterodiaryl, and cyclic ketones in good to excellent yields. Moreover, the oxidative cleavage of C-C triple bonds from 1-alkynes is demonstrated for the synthesis of symmetrical and unsymmetrical ketones from the Cu-catalyzed [3+2]-cycloaddition, Rh-catalyzed alkoxyarylation, photooxygenation, and ring-opening reaction in one-pot. Because the synthesis of the symmetrical and unsymmetrical diaryl and/or heterodiaryl ketones bearing an electron-donating group is not easy, the present method is notable.
- Kim, Hyunseok,Park, Sangjune,Baek, Yonghyeon,Um, Kyusik,Han, Gi Uk,Jeon, Da-Hye,Han, Sang Hoon,Lee, Phil Ho
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p. 3486 - 3496
(2018/04/14)
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- Synthesis of 1-Alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones through Gold/Bronsted Acid Relay Actions: Observation of Selective C=C Bond Cleavage of Enaminones
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A novel gold(I)/Bronsted acid sequential catalyzed/promoted procedure to synthesize 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones under mild reaction conditions is developed. This methodology is realized by relay actions of gold and a Bronsted acid in a one-pot multistep manner. The gold(I)-catalyzed chemoselective C(sp 2)-H functionalization of enaminones and Bronsted acid promoted cleavage of the C=C bond are integrated effectively. Based on the results of control experiments and ESI-MS analysis, a possible reaction mechanism is proposed.
- Zhao, Yulei,Yuan, Yang,Kong, Lingkai,Zhang, Fangfang,Li, Yanzhong
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p. 3609 - 3618
(2017/08/15)
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- Synthesis of Azulen-1-yl Ketones via Oxidative Cleavage of C-C Multiple Bonds in N-Sulfonyl Enamides and 1-Alkynes under Air and Natural Sunlight
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A synthetic method to prepare azulen-1-yl ketones was developed via oxidative cleavage of the C-C double bond in the reaction of easily obtainable N-sulfonyl enamides with Cs2CO3 under air and natural sunlight and in the absence of a photosensitizer. Oxidative cleavage of C-C triple bonds was also demonstrated for the synthesis of azulen-1-yl ketones via a tandem Cu-catalyzed [3 + 2] cycloaddition, Rh-catalyzed arylation, photooxygenation, and ring-opening reaction in one pot under air and natural sunlight.
- Park, Sangjune,Jeon, Woo Hyung,Yong, Woo-Soon,Lee, Phil Ho
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supporting information
p. 5060 - 5063
(2015/11/03)
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- Synthesis of ynamides from formamides
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N-Formyl-tosylamides can be efficiently converted to N-ethynyl-tosylamides in two steps via the corresponding dichlorovinylamides.
- Brückner, David
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p. 3809 - 3814
(2007/10/03)
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- Stereoselective synthesis of alcohols. Part LV. Domino hydroformylation-allylboration-hydroformylation reactions to give trans-perhydropyrano[3,2-b] pyridine derivatives
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N-Allyl-(E)-γ-aminoallyl boronates 8 and 18, when subjected to hydroformylation conditions, enter into a domino hydroformylation-allylboration-hydroformylation reaction cascade to generate the bicyclic N,O-heterocycles 12 and 20. On reaction of the methal
- Hoffmann,Brueckner
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p. 369 - 373
(2007/10/03)
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- DECOMPOSITION OF ARILAZIDES AND P-TOSYLAZIDE BY THF/n-BUTYLLITHIUM. A NEW SOURCE OF DIAZOMETHANE
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Variously substituted arylazides, as well as p-tosylazide, when allowed to react at room temperature with THF previously treated with n-butyllithium, undergo a rapid decomposition affording the corresponding amines and formamides, together with diazomethane.This diazo transfer (with deformylation) reaction is thought to involve the enolate of the acetaldehyde generated by the known cycloreversion of THF in the presence on n-butyllithium.
- Babudri, F.,Di Nunno, L.,Florio, S.,Valzano, S.
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p. 1731 - 1736
(2007/10/02)
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