Telomerization reactions of butadiene and CO2 catalyzed by phosphine Pd(0) complexes: (E)-2-ethylidenehept-6-en-5-olide and octadienyl esters of 2-ethylidenehepta-4,6-dienoic acid

Musco, A.; Perego, Carlo; TARTIARI, V.

doi:10.1016/s0020-1693(00)87385-5

Cited by 122 publications

(59 citation statements)

References 7 publications

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“…Much pioneering work on catalytic CO 2 chemistry was conducted around the world including the groups of Behr [22 -27], Hoberg [28 -35], Walther [36,37], and Dinjus [38 -42], as well as Inoue [43 -47], Musco [48], Yamamoto [49,50], Darensbourg [51,52], and others [53 -57]. These efforts have developed a fundamental understanding of the chemistry of metal complexes with CO 2 providing a sound basis for the rational development of catalytic transformations of this raw material.…”

Section: Reactivity Of Co 2 At Metal Centersmentioning

confidence: 99%

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

Hölscher

Gürtler

Keim

et al. 2012

Zeitschrift Für Naturforschung B

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Dedicated to Professor Heribert Offermanns on the occasion of his 75 th birthdayWith the growing perception of industrialized societies that fossil raw materials are limited resources, academic chemical research and chemical industry have started to introduce novel catalytic technologies which aim at the development of economically competitive processes relying much more strongly on the use of alternative carbon feedstocks. Great interest is given world-wide to carbon dioxide (CO 2 ) as it is part of the global carbon cycle, nontoxic, easily available in sufficient quantities anywhere in the industrialized world, and can be managed technically with ease, and at low cost. In principle carbon dioxide can be used to generate a large variety of synthetic products ranging from bulk chemicals like methanol and formic acid, through polymeric materials, to fine chemicals like aromatic acids useful in the pharmaceutical industry. Owing to the high thermodynamic stability of CO 2 , the energy constraints of chemical reactions have to be carefully analyzed to select promising processes. Furthermore, the high kinetic barriers for incorporation of CO 2 into C-H or C-C bond forming reactions require that any novel transformation of CO 2 must inevitably be associated with a novel catalytic technology. This short review comprises a selection of the most recent academic and industrial research developments mainly with regard to innovations in CO 2 chemistry in the field of homogeneous catalysis and processes.

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Section: Reactivity Of Co 2 At Metal Centersmentioning

confidence: 99%

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

Hölscher

Gürtler

Keim

et al. 2012

Zeitschrift Für Naturforschung B

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“…13 C NMR (CDCl 3 , 100.6 MHz): d = 138.6, 138.6 (C-2,2'); 134. 1,6');127.1,7');114.5,1');73.8 (OCH 2 CHMe);73.5 (CHMe);72.0,8');33.2,3');5');28.3,4') Me). 13 C NMR (CDCl 3 , 100.6 MHz): d = 138.6, 138.6 (C-2,2'); 134.0, 133.6 (C-6,6'); 127.…”

Section: General Procedures For the Telomerization Of Butadiene With Dunclassified

“…13 C NMR (CDCl 3 , 100.6 MHz): d = 138.6, 138.6 (C-2,2'); 134.0, 133.6 (C-6,6'); 127. 2, 126.8 (C-7,7 (m,6 H,5,CH 2(cHex) ); 2 H,CH 2(cHex) ); 1.47 (m, 2 H, H-4); 4 H,2 CH 2(cHex) ). 13 C NMR (CDCl 3 , 75.5 MHz): d = 138.5 (C-2); 134.2 (C-6); 126.8 (C-7); 114.5 (C-1); 82.9, 73.6 (CHOH, CHO); 69.5 (C-8); 33.1 (C-3); 32.0 (CH 2(cHex) ); 31.6 (C-5); 29.2 (CH 2(cHex) ); 28.1 (C-4); 24.2, 23.9 ppm (2 CH 2(cHex) C NMR (CDCl 3 , 100.6 MHz): d = 138.6, 138.6 (C-2,2'); 133.9, 133.5 (C-6,6'); 127.3, 126.8 (C-7,7'); 114.5, 114.5 (C-1,1'); 74.3 (CHMe); 71.…”

Section: General Procedures For the Telomerization Of Butadiene With Dmentioning

confidence: 99%

“…Typical examples of 100 % atom-efficient catalytic reactions include the addition of nucleophiles to olefins and alkynes. Among these reactions, the dimerization of two molecules of a 1,3-diene with appropriate nucleophiles (HX) [1] such as alcohols, [2] amines, [3] water, [4] and carbon dioxide [5] to give functionalized octadienes is generally known as the telomerization reaction. This synthetic methodology was independently discovered in 1967 by Smutny and Takahashi.…”

Section: Introductionmentioning

confidence: 99%

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Efficient and Selective Telomerization of 1,3‐Butadiene with Diols Catalyzed by Palladium–Carbene Complexes

et al. 2009

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The selective telomerization of 1,3-butadiene with seven different linear and cyclic diols proceeds in the presence of in situ generated palladium carbene catalysts. By applying optimized reaction conditions, including very low metal loadings (2-10 ppm), excellent catalyst turnover numbers (>250,000) and good chemoselectivities are observed with respect to the mono-octadienyl ether derivatives. This protocol allows the efficient preparation of unsaturated alcohols, which are useful for various applications.

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“…Die ersten Untersuchungen zur Umsetzung von 1,3-Butadien mit CO 2 wurden in den Arbeitsgruppen von Inoue [118] und Musco [119] durchgeführt. Sie synthetisierten Lactone (32-34), 1,3,7-Octatrien (35), Carbonsäuren (36, 37) und Ester (38, 39) in kleinen Mengen.…”

Section: Telomerisation Von 13-butadien Mit Counclassified

Telomerisation – Fortschritte und Anwendungen einer vielseitigen Reaktion

et al. 2009

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Wandelbar wie ein Chamäleon: Die übergangsmetallkatalysierte Telomerisation von 1,3‐Dienen mit verschiedenen Nucleophilen führt zur zahlreichen Produkten, die sowohl in Kosmetika und Pharmaka als auch in Polymeren und Duftstoffen Anwendung finden. Der Aufsatz gibt einen Überblick über diese vielseitige Reaktion mit Bezug auf die aktuelle Forschung und industrielle Anwendungen.magnified imageDurch übergangsmetallkatalysierte Telomerisation von 1,3‐Dienen mit verschiedenen Nucleophilen lassen sich zahlreiche funktionalisierte Kohlenwasserstoffe synthetisieren, z. B. Zuckerether, substituierte Lactone oder Terpenderivate, die in Kosmetika und pharmazeutischen Produkten sowie in Polymeren und Aromastoffen Anwendung finden. Die Reaktion kann durch die Wahl des Katalysatorsystems, der Reaktanten und der Reaktionsbedingungen gesteuert werden. Seit der Entdeckung der Telomerisation im Jahr 1967 gab es viele Ansätze zur Nutzung der Reaktion. In diesem Aufsatz wird anhand von Beispielen aus Forschung und Industrie die Vielseitigkeit dieser Reaktion verdeutlicht, wobei besonders auf Katalysator‐ und Prozessentwicklungen sowie ausgewählte mechanistische Aspekte eingegangen wird.

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Telomerization reactions of butadiene and CO2 catalyzed by phosphine Pd(0) complexes: (E)-2-ethylidenehept-6-en-5-olide and octadienyl esters of 2-ethylidenehepta-4,6-dienoic acid

Cited by 122 publications

References 7 publications

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

Efficient and Selective Telomerization of 1,3‐Butadiene with Diols Catalyzed by Palladium–Carbene Complexes

Telomerisation – Fortschritte und Anwendungen einer vielseitigen Reaktion

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