ChemInform Abstract: Metal-Free Aerobic Oxidative C-N Bond Cleavage of Tertiary Amines for the Synthesis of N-Heterocycles with High Atom Efficiency.

ChemInform ◽  
2014 ◽  
Vol 45 (44) ◽  
pp. no-no
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Daoqing Han ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Tertiary Amines ◽  
Metal Free

Metal-free aerobic oxidative C–N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency

2014 ◽  
Vol 12 (23) ◽  
pp. 3802-3807 ◽  
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Daoqing Han ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Tertiary Amines ◽  
Metal Free ◽  
Alkyl Groups

An efficient metal-free aerobic C–N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency. All of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles.

ChemInform Abstract: Iodine-Catalyzed C3-Formylation of Indoles via C-N Bond Cleavage of Tertiary Amines under Aerobic Conditions.

ChemInform ◽  
2015 ◽  
Vol 46 (37) ◽  
pp. no-no
Author(s):  
Lin Lu ◽  
Qiheng Xiong ◽  
Shengmei Guo ◽  
Tianqiang He ◽  
Feng Xu ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Tertiary Amines ◽  
Aerobic Conditions

Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Synthesis ◽  
2021 ◽  
Author(s):  
Wey-Chyng Jeng ◽  
Po-Chung Chien ◽  
Sandip Sambhaji Vagh ◽  
Athukuri Edukondalu ◽  
Wenwei Lin
Keyword(s):  
Intramolecular Cyclization ◽  
Efficient Method ◽  
Bond Cleavage ◽  
Scale Up ◽  
Acyl Chlorides ◽  
Metal Free ◽  
Mild Conditions ◽  
Synthetic Utility ◽  
Mechanistic Investigations ◽  
Synthetic Transformations

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides in the presence of base-catalyzed by organophosphanes. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under metal-free and mild conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/ rearrangement sequence. The mechanistic investigations revealed that the C-O bond cleavage on possible betaine intermediate is the key step for the installation of keto-functionality at β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by scale-up reactions and synthetic transformations of the products.

ChemInform Abstract: DIAD-Mediated Metal-Free Cross Dehydrogenative Coupling Between Tertiary Amines and α-Fluorinated Sulfones.

ChemInform ◽  
2013 ◽  
Vol 44 (44) ◽  
pp. no-no
Author(s):  
Weizhou Huang ◽  
Chuanfa Ni ◽  
Yanchuan Zhao ◽  
Jinbo Hu
Keyword(s):  
Tertiary Amines ◽  
Metal Free ◽  
Dehydrogenative Coupling

Pd/C-catalyzed synthesis of oxamates by oxidative cross double carbonylation of alcohols and tertiary amines through C–N bond cleavage

2019 ◽  
Vol 43 (46) ◽  
pp. 18072-18078 ◽  
Author(s):  
Yuvraj A. Kolekar ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Active Compound ◽  
Bond Cleavage ◽  
Tertiary Amines ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
Biological Active Compound

Palladium-catalyzed oxidative cross double carbonylation reaction between tertiary amines and alcohols using oxidant O2 and KI as the additive affords oxamates. Oxamate are as a intermediate in biological active compound and glycol synthesis.

I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2018-2023 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Tongle Shao ◽  
Jun Zhou ◽  
Chen Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Oxidation Pathway ◽  
Keto Esters ◽  
Oxidative Coupling Reaction

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

scholarly journals Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transfer Reaction ◽  
Bond Cleavage ◽  
Electron Transfer Reaction ◽  
Amide Bond ◽  
Single Electron Transfer ◽  
Reaction Conditions ◽  
Metal Free ◽  
Single Electron Transfer Reaction

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.

scholarly journals Na2CO3-promoted thioesterification via N–C bond cleavage of amides to construct thioester derivatives

2019 ◽  
Vol 43 (11-12) ◽  
pp. 486-492
Author(s):  
Jiasi Tao ◽  
Weijie Yu ◽  
Jin Luo ◽  
Tao Wang ◽  
Wanling Ge ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Metal Free

A mild, efficient, and transition-metal-free catalytic strategy is developed to construct thioesters via selective N–C bond cleavage of Boc2-activated primary amides. This strategy is successfully carried out with stoichiometric Na2CO3 as the base and provides the corresponding products in moderate to excellent yields.

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