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TMSOTf-Promoted Addition of Alkynes to Aldehydes: A Novel Synthesis of Chroman-4-ones
Park, Ji Yeon,Ullapu, Punna Reddy,Choo, Hyunah,Lee, Jae Kyun,Min, Sun-Joon,Pae, Ae Nim,Kim, Youseung,Baek, Du-Jong,Cho, Yong Seo WILEY-VCH Verlag 2008 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Vol.2008 No.32
<P>A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)</P> <B>Graphic Abstract</B> <P>A novel synthetic method to prepare chalcones and chroman-4-ones by TMSOTf-promoted addition of alkynes to various aldehydes has been developed. The ratios of chalcones, chroman-4-ones and hydratedproducts vary depending upon the substituents on the alkynes. We also describe the transformation of the chalcones to the corresponding chroman-4-ones under basic conditions. <img src='wiley_img/1434193X-2008-2008-32-EJOC200800782-fig000.gif' alt='wiley_img/1434193X-2008-2008-32-EJOC200800782-fig000'> </P>
Lee, Sumin,Li, Dingxi,Yun, Jaesook Wiley-VCH 2014 Chemistry - An Asian Journal Vol.9 No.9
<P>The copper-catalyzed sequential hydroboration of terminal alkynes with pinacolborane to prepare 1,1-diborylalkanes directly from alkynes was studied. Protected propargyl amines, propargyl alcohol derivatives, and simple alkynes regioselectively produced the desired 1,1-diborylalkanes in good yields with a copper/xantphos catalyst.</P>
Chaugule, Avinash A.,Tamboli, Ashif H.,Kim, Hern Elsevier 2017 CHEMICAL ENGINEERING JOURNAL -LAUSANNE- Vol.326 No.-
<P><B>Abstract</B></P> <P>The carboxylation of terminal alkynes from CO<SUB>2</SUB> is a most attractive route in green chemistry point of view. Herein, we synthesized a novel CuCl<SUB>2</SUB>@Poly-GLY(1-Vim)<SUB>3</SUB>(OMs)<SUB>3</SUB> catalyst and employed to the efficient carboxylation of terminal alkynes (phenyl carboxylate esters) by utilizing CO<SUB>2</SUB> under 4MPa, at 40°C. In presence of catalyst, various terminal alkynes found to be easily reacting with CO<SUB>2</SUB> and organic halide to affording a high yield of carboxylic ester. Moreover, CuCl<SUB>2</SUB>@Poly-GLY(1-vim)<SUB>3</SUB>(OMs)<SUB>3</SUB> catalyst is capable to obtain a high yield of corresponding carboxylic ester using various types organic halide. Furthermore, CuCl<SUB>2</SUB>@Poly-GLY(1-vim)<SUB>3</SUB>(OMs)<SUB>3</SUB> catalyst able to easily recover and reuse for four times without any obvious loss in catalytic activity. The catalytic reactivity of CuCl<SUB>2</SUB>@Poly-GLY(1-vim)<SUB>3</SUB>(OMs)<SUB>3</SUB> catalyst is explained on the basis of predicted mechanism.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Preparation of Poly-GLY(mim)<SUB>3</SUB>(OMs)<SUB>3</SUB>. </LI> <LI> Synthesis of Cu@Poly-GLY(mim)<SUB>3</SUB>(OMs)<SUB>3</SUB> catalyst. </LI> <LI> Efficient carboxylation of terminal alkyne. </LI> <LI> Catalyst able to reuse for four times. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Platinum-Catalyzed Hydrogenative Cyclization of Yne-Enones, Yne-Aldehydes, and Yne-Dienes
Shinde, Mahadev P.,Wang, Xi,Kang, Eun Joo,Jang, Hye-Young WILEY-VCH Verlag 2009 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Vol.2009 No.35
<P>Pt complexes were used in the presence of phosphane ligands, SnCl<SUB>2</SUB>, and H<SUB>2</SUB> for coupling reactions of alkynes with electrophiles under environmentally benign hydrogenation conditions, providing five- and six-membered cycloreduction products in moderate to good yield. Deuterium labeling studies suggested the occurrence of a catalytic cycle including the diploar intermediate derived from hydrometalation of a platinum–hydride complex to the alkyne. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</P> <B>Graphic Abstract</B> <P>Using Pt<SUP>II</SUP> complexes and hydrogen, the reductive cyclizations of yne-enones, yne-aldehydes, and yne-dienes were conducted, which showed expanded reactivity of the Pt–alkyne complex with various electrophiles. <img src='wiley_img/1434193X-2009-2009-35-EJOC200901005-fig000.gif' alt='wiley_img/1434193X-2009-2009-35-EJOC200901005-fig000'> </P>
루테늄 지르코니아 불균일 촉매를 이용한 알켄 또는 알킨의 효과적인 산화절단반응
모비나이르샤드 ( Mobina Irshad ),최봉길 ( Bong Gill Choi ),강온유 ( Onyu Kang ),홍석복 ( Seok Bok Hong ),황성연 ( Sung Yeon Hwang ),허영민 ( Young Min Heo ),김정원 ( Jung Won Kim ) 한국공업화학회 2016 공업화학 Vol.27 No.6
알켄 또는 알킨의 산화 반응이 루테늄 지르코니아 불균일 촉매에 의해 매우 선택적이며 효율적으로 전환되었다. 절단반응을 통해, C-C 이중 결합은 알데히드 관능기로, 삼중 결합은 다이케톤 또는 카르복시산으로 전환되었는데, 다양한 기질들이 30 ℃에서 PhI(OAc)<sub>2</sub> 산화제와 dichloromethane 및 물(각각 5 mL와 0.5 mL)의 혼합 용매 조건에서 반응이 수행되었다. 사용된 촉매 Ru(OH)<sub>x</sub>/ZrO<sub>2</sub>는 이 절단 반응에 대해 기존의 다른 루테늄 기반 불균일 또는 균일 촉매들보다 더 좋은 활성과 선택성을 보였다. 반응이 진행되는 동안, 제조된 촉매의 기계적인 물성은 안정적이었고, 금속의 침출은 전혀 보이지 않았다. 불포화된 탄화수소들의 산화적 절단에 대해, 합성된 촉매는 여러 번 재사용해도 그 촉매의 성능을 그대로 유지하였다. The efficiency of a heterogeneous ruthenium zirconia catalyst (Ru(OH)<sub>x</sub>/ZrO<sub>2</sub>) was demonstrated to the selective oxidative transformation of alkenes or alkynes. The scissions of C-C double bonds to aldehydes and triple bonds to diketones or carbox-ylic acids were carried out with (diacetoxyiodo)benzene as an oxidant under dichloromethane (5 mL)/water (0.5 mL) solvent system at 30 ℃ for wide range of substrates. The Ru(OH)<sub>x</sub>/ZrO<sub>2</sub> composite showed higher catalytic activity and selectivity than other ruthenium-based homogeneous or heterogeneous catalysts for the scission reaction. The catalyst exhibited a high mechanical stability, and no leaching of the metal was observed during the reaction. These features ensured the reusability of the catalyst for several times for the oxidative cleavage of unsaturated hydrocarbons.
Synthesis of Tetracyclic 5-Azaindole Analogues by Palladium-Catalyzed Sequential Annulation
Sung, Nack-Do,Yang, Ok-Kyung,Kang, Song-Su,Yum, Eul-Kgun Korean Chemical Society 2004 Bulletin of the Korean Chemical Society Vol.25 No.9
Tetracyclic 5-azaindole analogues were prepared by palladium-catalyzed sequential annulation of benzylidene(3-iodopyridinyl-4-yl)amine and 1-aryl substituted internal alkynes under $Pd(OAc)_2,\;n-Bu_4NCl,\;and Et_3N\;at\;120^{\circ}C.$ The synthetic procedure showed possible diversification of tetracyclic 5-azaindole analogues by varying the 1-aryl substituent in internal alkynes.
Synthesis of Tetracyclic 5-AzaIndole Analogues by Palladium-Catalyzed Sequential Annulation
Sung, Nack-Do,Yang, Ok-kyung,kang, Song Su,Yum, Eul Kgun 충남대학교 형질전환복제돼지연구센터 2004 논문집 Vol. No.8
Tetracyclic 5-azaindole analogues were prepared by palladium-catalyzed sequential annulation of benzyl-idene(3-iodopyridinyl-4-yl)amine and l-aryl substituted internal alkynes under Pd(OAc)₂, n-Bu₄NCl, and Ft₃N at 120℃. The synthetic procedure showed possible diversification of tetracyclic 5-azaindole analogues by varying the l-aryl substituent in internal alkynes.
Iridium(I)-Catalyzed Cycloisomerization of Cyclohexadienyl Alkynes
Sim, So Hee,Lee, Sang Ick,Park, Ji Hoon,Chung, Young Keun WILEY-VCH Verlag 2010 Advanced synthesis & catalysis Vol.352 No.2
<P>From cyclohexadienyl alkynes with a terminal alkyne unit, double cyclopropanated products were obtained in reasonable to high yields. For cyclohexadienyl alkynes substituted at the alkyne unit, cyclopropanated products were obtained in high yields. When a keto carbonyl group was introduced to cyclohexadienyl alkynes with a substituted alkyne, Alder-ene-type products were obtained in reasonable to high yields.</P> <B>Graphic Abstract</B> <P> <img src='wiley_img/16154150-2010-352-2-3-ADSC200900578-content.gif' alt='wiley_img/16154150-2010-352-2-3-ADSC200900578-content'> </P>
Efficient catalytic system for carboxylation of alkynes employing carbon dioxide
( Mujmule Rajendra Basavant ),김헌 한국공업화학회 2019 한국공업화학회 연구논문 초록집 Vol.2019 No.0
Carbon dioxide utilization has attracted great attention from researchers due to environmental problems and global warming. However, conversion of CO<sub>2</sub> is a great challenge due to the thermodynamic stability and kinetic inertness of CO<sub>2</sub>. With the increasing awareness of the ever-growing carbon dioxide levels in the atmosphere, great effort has been made to develop strategies and technologies towards the reduction of carbon emission. In this work, we have introduced efficient ionic liquid based catalytic system for the carboxylation of alkynes with CO<sub>2</sub> under mild reaction condition to produce the corresponding carboxylic esters. In addition, various parameters such as reaction temperature, pressure, reaction time, and reusability of catalyst are investigated.