publication . Article . 2017

Catalytic transformation of functionalized carboxylic acids using multifunctional rhenium complexes.

Masayuki Naruto; Santosh Agrawal; Katsuaki Toda; Susumu Saito;
Open Access English
  • Published: 13 Jun 2017 Journal: Scientific Reports, volume 7 (eissn: 2045-2322, Copyright policy)
  • Publisher: Nature Publishing Group UK
Abstract
Carboxylic acids (CAs) are one of the most ubiquitous and important chemical feedstocks available from biorenewable resources, CO2, and the petrochemical industry. Unfortunately, chemoselective catalytic transformations of CH n CO2H (n = 1–3) groups into other functionalities remain a significant challenge. Herein, we report rheniumV complexes as extremely effective precatalysts for this purpose. Compared to previously reported heterogeneous and homogeneous catalysts derived from high- or low-valent metals, the present method involves a α-C–H bond functionalization, a hydrogenation, and a hydrogenolysis, which affords functionalized alcohols with a wide substrat...
Subjects
free text keywords: Article, Rhenium, chemistry.chemical_element, chemistry, Surface modification, Petrochemical, Catalysis, Chemoselectivity, Hydrogenolysis, Combinatorial chemistry, Metal, visual_art.visual_art_medium, visual_art, Substrate (chemistry)
55 references, page 1 of 4

Wang, W-H, Himeda, Y, Muckerman, JT, Manbeck, GF, Fujita, E. CO2 hydrogenation to formate and methanol as an alternative to photo- and electrochemical CO2 reduction. Chem. Rev.. 2015; 115: 12936-12973 [OpenAIRE] [PubMed] [DOI]

Liu, Q, Wu, L, Jackstell, R, Beller, M. Using carbon dioxide as a building block in organic synthesis. Nat. Commun.. 2015; 6: 5933 [OpenAIRE] [PubMed] [DOI]

Otto, A, Grube, T, Schiebahn, S, Stolten, D. Closing the loop: captured CO2 as a feedstock in the chemical industry. Energy Environ. Sci.. 2015; 8: 3283-3297 [DOI]

Ostapowicz, TG, Schmitz, M, Krystof, M, Klankermayer, J, Leitner, W. Carbon dioxide as a C1 building block for the formation of carboxylic acids by formal catalytic hydrocarboxylation. Angew. Chem. Int. Ed.. 2013; 52: 12119-12123 [OpenAIRE] [DOI]

Masuda, Y, Ishida, N, Murakami, M. Light-driven carboxylation of o‑alkylphenyl ketones with CO2. J. Am. Chem. Soc.. 2015; 137: 14063-14066 [OpenAIRE] [PubMed] [DOI]

Arai, T, Sato, S, Morikawa, T. A monolithic device for CO2 photoreduction to generate liquid organic substances in a single-compartment reactor. Energy Environ. Sci.. 2015; 8: 1998-2002 [DOI]

Sato, S. Selective CO2 conversion to formate conjugated with H2O oxidation utilizing semiconductor/complex hybrid photocatalysts. J. Am. Chem. Soc.. 2011; 133: 15240-15243 [OpenAIRE] [PubMed] [DOI]

Ruppert, AM, Weinberg, K, Palkovits, R. Hydrogenolysis goes bio: from carbohydrates and sugar alcohols to platform chemicals. Angew. Chem. Int. Ed.. 2012; 51: 2564-2601 [OpenAIRE] [DOI]

Corma, A, Iborra, S, Velty, A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev.. 2007; 107: 2411-2502 [PubMed] [DOI]

Bozell, JJ, Petersen, GR. Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited. Green Chem.. 2010; 12: 539-554 [DOI]

Olah, GA, Prakash, GKS, Goeppert, A. Anthropogenic chemical carbon cycle for a sustainable future. J. Am. Chem. Soc.. 2011; 133: 12881-12898 [OpenAIRE] [PubMed] [DOI]

Teichmann, D, Arlt, W, Wasserscheid, P, Freymann, R. A future energy supply on liquid organic hydrogen carriers (LOHC). Energy Environ. Sci.. 2011; 4: 2767-2773 [OpenAIRE] [DOI]

Stöcker, M. Biofuels and biomass-to-liquid fuels in the biorefinery: catalytic conversion of lignocellulosic biomass using porous materials. Angew. Chem. Int. Ed.. 2008; 47: 9200-9211 [OpenAIRE] [DOI]

Watanabe, R, Yamauchi, M, Sadakiyo, M, Abe, R, Takeguchi, T. CO2-free electric power circulation via direct charge and discharge using the glycolic acid/oxalic acid redox couple. Energy Environ. Sci.. 2015; 8: 1456-1462 [DOI]

Morita, Y, Yamamoto, T, Nagai, H, Shimizu, Y, Kanai, M. Chemoselective boron-catalyzed nucleophilic activation of carboxylic acids for Mannich-type reactions. J. Am. Chem. Soc.. 2015; 137: 7075-7078 [OpenAIRE] [PubMed] [DOI]

55 references, page 1 of 4
Abstract
Carboxylic acids (CAs) are one of the most ubiquitous and important chemical feedstocks available from biorenewable resources, CO2, and the petrochemical industry. Unfortunately, chemoselective catalytic transformations of CH n CO2H (n = 1–3) groups into other functionalities remain a significant challenge. Herein, we report rheniumV complexes as extremely effective precatalysts for this purpose. Compared to previously reported heterogeneous and homogeneous catalysts derived from high- or low-valent metals, the present method involves a α-C–H bond functionalization, a hydrogenation, and a hydrogenolysis, which affords functionalized alcohols with a wide substrat...
Subjects
free text keywords: Article, Rhenium, chemistry.chemical_element, chemistry, Surface modification, Petrochemical, Catalysis, Chemoselectivity, Hydrogenolysis, Combinatorial chemistry, Metal, visual_art.visual_art_medium, visual_art, Substrate (chemistry)
55 references, page 1 of 4

Wang, W-H, Himeda, Y, Muckerman, JT, Manbeck, GF, Fujita, E. CO2 hydrogenation to formate and methanol as an alternative to photo- and electrochemical CO2 reduction. Chem. Rev.. 2015; 115: 12936-12973 [OpenAIRE] [PubMed] [DOI]

Liu, Q, Wu, L, Jackstell, R, Beller, M. Using carbon dioxide as a building block in organic synthesis. Nat. Commun.. 2015; 6: 5933 [OpenAIRE] [PubMed] [DOI]

Otto, A, Grube, T, Schiebahn, S, Stolten, D. Closing the loop: captured CO2 as a feedstock in the chemical industry. Energy Environ. Sci.. 2015; 8: 3283-3297 [DOI]

Ostapowicz, TG, Schmitz, M, Krystof, M, Klankermayer, J, Leitner, W. Carbon dioxide as a C1 building block for the formation of carboxylic acids by formal catalytic hydrocarboxylation. Angew. Chem. Int. Ed.. 2013; 52: 12119-12123 [OpenAIRE] [DOI]

Masuda, Y, Ishida, N, Murakami, M. Light-driven carboxylation of o‑alkylphenyl ketones with CO2. J. Am. Chem. Soc.. 2015; 137: 14063-14066 [OpenAIRE] [PubMed] [DOI]

Arai, T, Sato, S, Morikawa, T. A monolithic device for CO2 photoreduction to generate liquid organic substances in a single-compartment reactor. Energy Environ. Sci.. 2015; 8: 1998-2002 [DOI]

Sato, S. Selective CO2 conversion to formate conjugated with H2O oxidation utilizing semiconductor/complex hybrid photocatalysts. J. Am. Chem. Soc.. 2011; 133: 15240-15243 [OpenAIRE] [PubMed] [DOI]

Ruppert, AM, Weinberg, K, Palkovits, R. Hydrogenolysis goes bio: from carbohydrates and sugar alcohols to platform chemicals. Angew. Chem. Int. Ed.. 2012; 51: 2564-2601 [OpenAIRE] [DOI]

Corma, A, Iborra, S, Velty, A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev.. 2007; 107: 2411-2502 [PubMed] [DOI]

Bozell, JJ, Petersen, GR. Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited. Green Chem.. 2010; 12: 539-554 [DOI]

Olah, GA, Prakash, GKS, Goeppert, A. Anthropogenic chemical carbon cycle for a sustainable future. J. Am. Chem. Soc.. 2011; 133: 12881-12898 [OpenAIRE] [PubMed] [DOI]

Teichmann, D, Arlt, W, Wasserscheid, P, Freymann, R. A future energy supply on liquid organic hydrogen carriers (LOHC). Energy Environ. Sci.. 2011; 4: 2767-2773 [OpenAIRE] [DOI]

Stöcker, M. Biofuels and biomass-to-liquid fuels in the biorefinery: catalytic conversion of lignocellulosic biomass using porous materials. Angew. Chem. Int. Ed.. 2008; 47: 9200-9211 [OpenAIRE] [DOI]

Watanabe, R, Yamauchi, M, Sadakiyo, M, Abe, R, Takeguchi, T. CO2-free electric power circulation via direct charge and discharge using the glycolic acid/oxalic acid redox couple. Energy Environ. Sci.. 2015; 8: 1456-1462 [DOI]

Morita, Y, Yamamoto, T, Nagai, H, Shimizu, Y, Kanai, M. Chemoselective boron-catalyzed nucleophilic activation of carboxylic acids for Mannich-type reactions. J. Am. Chem. Soc.. 2015; 137: 7075-7078 [OpenAIRE] [PubMed] [DOI]

55 references, page 1 of 4
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publication . Article . 2017

Catalytic transformation of functionalized carboxylic acids using multifunctional rhenium complexes.

Masayuki Naruto; Santosh Agrawal; Katsuaki Toda; Susumu Saito;