B(C6F5)3-catalyzed metal-free hydrogenation of naphthylamines

2015 ◽  
Vol 13 (10) ◽  
pp. 2875-2878 ◽  
Author(s):  
Gen Li ◽  
Yongbing Liu ◽  
Haifeng Du
Keyword(s):  
Metal Free ◽  
Mild Conditions ◽  
Catalytic Metal ◽  
High Yields ◽  
First Time

A catalytic metal-free hydrogenation of naphthylamines using B(C6F5)3 was achieved under mild conditions for the first time to furnish tetrahydronaphthylamines in high yields.

Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C–C and C–N bonds

RSC Advances ◽  
2015 ◽  
Vol 5 (121) ◽  
pp. 100102-100105 ◽  
Author(s):  
Kelu Yan ◽  
Daoshan Yang ◽  
Wei Wei ◽  
Guoqing Li ◽  
Mingyang Sun ◽  
...  
Keyword(s):  
Ring Opening ◽  
Metal Free ◽  
Mild Conditions ◽  
First Time

A highly regioselective TBHP-mediated ring opening of imidazopyridinesviacleavage of C–C and C–N bonds has been realized for the first time to afford usefulN-(pyridin-2-yl)benzamides under mild conditions.

scholarly journals Microporous polyurethane material for size selective heterogeneous catalysis of the Knoevenagel reaction

2016 ◽  
Vol 52 (50) ◽  
pp. 7834-7837 ◽  
Author(s):  
Sandeep Kumar Dey ◽  
Nader de Sousa Amadeu ◽  
Christoph Janiak
Keyword(s):  
Heterogeneous Catalysis ◽  
Knoevenagel Reaction ◽  
Bond Forming ◽  
Mild Conditions ◽  
Bond Forming Reactions ◽  
Type C ◽  
High Yields ◽  
First Time

For the first time, a microporous polyurethane (MPU) is prepared – it acts as an organocatalyst for aldol-type C–C bond forming reactions with high yields and under mild conditions.

Metal–metal redox synergy in selective B–H activation of ortho-carborane-9,12-dithiolate

2014 ◽  
Vol 50 (86) ◽  
pp. 13077-13080 ◽  
Author(s):  
Xiaolei Zhang ◽  
Zhiwen Zhou ◽  
Hong Yan
Keyword(s):  
Mild Conditions ◽  
Metal Metal ◽  
High Yields ◽  
Metal Redox ◽  
First Time

Metal–metal redox synergy is introduced, for the first time, for B–H functionalization of inert dicarba-dodecaboranes under mild conditions in high yields.

scholarly journals Mild Deprotection of Dithioacetals by TMSCl / NaI Association in CH3CN

2020 ◽  
Author(s):  
Olivier Provot ◽  
Yunxin Yao ◽  
Guangkuan Zhao ◽  
Abdallah Hamze ◽  
Mouad Alami
Keyword(s):  
Good Alternative ◽  
Experimental Conditions ◽  
Metal Free ◽  
Free Process ◽  
High Yields ◽  
First Time ◽  
Carbonyl Function

<p><a>We showed for the first time, the fundamental role<b> </b>of CH<sub>3</sub>CN associated to TMSCl/NaI combination to deprotect S,S-ethylene- and S,S-propylene-ketals into ketones. Indeed, if the TMSCl/NaI association leads to the reduction of dithioketals in CH<sub>2</sub>Cl<sub>2</sub>, we have demonstrated that this association can be used to deprotect a large variety of various dithioketals into ketones in CH<sub>3</sub>CN. Otherwise, under mild experimental conditions, O,O-acetals as well as O,S-oxathianes were cleanly deprotected with high yields. It is also possible to easily regenerate the carbonyl function of various hydrazones and imines using this novel protocol. We believe that this metal-free process is a good alternative to other known methodologies used to deprotect dithioketals into ketones.<b></b></a></p><table></table><br>

scholarly journals Hydrogen-bond donor and acceptor cooperative catalysis strategy for cyclic dehydration of diols to access O-heterocycles

2021 ◽  
Vol 7 (22) ◽  
pp. eabg0396
Author(s):  
Huan Wang ◽  
Yanfei Zhao ◽  
Fengtao Zhang ◽  
Zhengang Ke ◽  
Buxing Han ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Free Acid ◽  
Hydrogen Bond Donor ◽  
Metal Free ◽  
Mild Conditions ◽  
Cooperative Catalysis ◽  
Donor And Acceptor ◽  
Green Strategy ◽  
High Yields ◽  
Better Than

Dehydrative cyclization of diols to O-heterocycles is attractive, but acid and/or metal-based catalysts are generally required. Here, we present a hydrogen-bond donor and acceptor cooperative catalysis strategy for the synthesis of O-heterocycles from diols in ionic liquids [ILs; e.g., 1-hydroxyethyl-3-methyl imidazolium trifluoromethanesulfonate ([HO-EtMIm][OTf])] under metal-free, acid-free, and mild conditions. [HO-EtMIm][OTf] is tolerant to a wide diol scope, shows performance even better than H2SO4, and affords a series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines, dioxanes, and thioxane in high yields. Mechanism investigation indicates that the IL cation and anion serve as hydrogen-bond donor and acceptor, respectively, to activate the C─O and O─H bonds of alcohol via hydrogen bonds, which synergistically catalyze dehydrative cyclization of diols to O-heterocycles. Notably, the products could be spontaneously separated after reaction because of their immiscibility with the IL, and the IL could be recycled. This green strategy has great potential for application in industry.

scholarly journals Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane

2016 ◽  
Vol 12 ◽  
pp. 2614-2619 ◽  
Author(s):  
Riccardo Porta ◽  
Alessandra Puglisi ◽  
Giacomo Colombo ◽  
Sergio Rossi ◽  
Maurizio Benaglia
Keyword(s):  
Continuous Flow ◽  
Reaction Times ◽  
Nitro Compounds ◽  
Primary Amines ◽  
Flow Conditions ◽  
Metal Free ◽  
Nitro Derivatives ◽  
Aromatic Nitro ◽  
High Yields ◽  
First Time

The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid).

Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines

2019 ◽  
Vol 21 (20) ◽  
pp. 5683-5690 ◽  
Author(s):  
Qing Yang ◽  
Yilin Zhang ◽  
Wei Zeng ◽  
Zheng-Chao Duan ◽  
Xinxin Sang ◽  
...  
Keyword(s):  
Free Base ◽  
Metal Free ◽  
Mild Conditions ◽  
Biomimetic Catalyst ◽  
Chemoselective Synthesis ◽  
Merrifield Resin ◽  
First Time

Metal-free, base-free, biomimetic, and chemoselective synthesis of 2,4,6-trisubstituted pyridines was developed for the first time under mild conditions.

scholarly journals Mild Deprotection of Dithioacetals by TMSCl / NaI Association in CH3CN

2020 ◽  
Author(s):  
Olivier Provot ◽  
Yunxin Yao ◽  
Guangkuan Zhao ◽  
Abdallah Hamze ◽  
Mouad Alami
Keyword(s):  
Good Alternative ◽  
Experimental Conditions ◽  
Metal Free ◽  
Free Process ◽  
High Yields ◽  
First Time ◽  
Carbonyl Function

<p><a>We showed for the first time, the fundamental role<b> </b>of CH<sub>3</sub>CN associated to TMSCl/NaI combination to deprotect S,S-ethylene- and S,S-propylene-ketals into ketones. Indeed, if the TMSCl/NaI association leads to the reduction of dithioketals in CH<sub>2</sub>Cl<sub>2</sub>, we have demonstrated that this association can be used to deprotect a large variety of various dithioketals into ketones in CH<sub>3</sub>CN. Otherwise, under mild experimental conditions, O,O-acetals as well as O,S-oxathianes were cleanly deprotected with high yields. It is also possible to easily regenerate the carbonyl function of various hydrazones and imines using this novel protocol. We believe that this metal-free process is a good alternative to other known methodologies used to deprotect dithioketals into ketones.<b></b></a></p><table></table><br>

A Borane-Catalyzed Metal-Free Hydrosilylation of Chromones and Flavones

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2421-2424 ◽  
Author(s):  
Haifeng Du ◽  
Xiaoyu Ren ◽  
Caifang Han ◽  
Xiangqing Feng
Keyword(s):  
Metal Free ◽  
High Yields ◽  
Asymmetric Transformation ◽  
First Time

A Piers-type hydrosilylation of chromones and flavones has been successfully realized for the first time using 0.1 mol % of borane catalyst generated in situ by hydroboration of pentafluorostyrene with HB(C6F5)2 to afford a variety of chromanones and flavanones in 60–99% yields. An attempt for the asymmetric transformation with chiral diyne and HB(C6F5)2 gave chromanones and flavanones in high yields with up to 32% ee.

An Expeditious One-Pot Three-Component Synthesis of 4-Aryl-3,4-dihydrobenzo[g] quinoline-2,5,10(1H)-triones under Green Conditions

2020 ◽  
Vol 23 (23) ◽  
pp. 2626-2634
Author(s):  
Saiedeh Kamalifar ◽  
Hamzeh Kiyani
Keyword(s):  
Reaction Medium ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
First Time ◽  
Green Conditions

: An efficient and facial one-pot synthesis of 4-aryl-3,4-dihydrobenzo[g]quinoline- 2,5,10(1H)-triones was developed for the first time. The process proceeded via the three-component cyclocondensation of 2-amino-1,4-naphthoquinone with Meldrum’s acid and substituted benzaldehydes under green conditions. The fused 3,4-dihydropyridin-2(1H)- one-ring naphthoquinones have been synthesized with good to high yields in refluxing ethanol as a green reaction medium. This protocol is simple and effective as well as does not involve the assistance of the catalyst, additive, or hazardous solvents.

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