Cobalt- and Rhodium-catalyzed Carboxylation Using Carbon Dioxide As the C1 Source

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2018 Oct 23

PMID 30344768

Citations 2

Authors

Tetsuaki Fujihara

Yasushi Tsuji

Affiliations

Soon will be listed here.

Abstract

Carbon dioxide (CO) is one of the most important materials as renewable chemical feedstock. In this review, the Co- and Rh-catalyzed transformation of CO via carbon-carbon bond-forming reactions is summarized. Combinations of metals (cobalt or rhodium), substrates, and reducing agents realize efficient carboxylation reactions using CO. The carboxylation of propargyl acetates and alkenyl triflates using cobalt complexes as well as the cobalt-catalyzed reductive carboxylation of α,β-unsaturated nitriles and carboxyamides in the presence of EtZn proceed. A Co complex has been demonstrated to act as an efficient catalyst in the carboxylation of allylic C(sp)-H bonds. Employing zinc as the reductant, carboxyzincation and the four-component coupling reaction between alkyne, acrylates, CO, and zinc occur efficiently. Rh complexes also catalyze the carboxylation of arylboronic esters, C(sp)-H carboxylation of aromatic compounds, and hydrocarboxylation of styrene derivatives. The Rh-catalyzed [2 + 2 + 2] cycloaddition of diynes and CO proceeds to afford pyrones.

Citing Articles

Cobalt-catalyzed reductive cross-coupling: a review.

Hassan S, Bilal M, Khalid S, Rasool N, Imran M, Shah A Mol Divers. 2024; .

PMID: 39466351 DOI: 10.1007/s11030-024-11017-1.

Electroreductive Cobalt-Catalyzed Carboxylation: Cross-Electrophile Electrocoupling with Atmospheric CO.

Ang N, Oliveira J, Ackermann L Angew Chem Int Ed Engl. 2020; 59(31):12842-12847.

PMID: 32329560 PMC: 7496797. DOI: 10.1002/anie.202003218.

References

Seo H, Katcher M, Jamison T . Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow. Nat Chem. 2017; 9(5):453-456. PMC: 5407320. DOI: 10.1038/nchem.2690. View

Prier C, Rankic D, MacMillan D . Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev. 2013; 113(7):5322-63. PMC: 4028850. DOI: 10.1021/cr300503r. View

Aresta M, Dibenedetto A, Angelini A . Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. technological use of CO2. Chem Rev. 2013; 114(3):1709-42. DOI: 10.1021/cr4002758. View

Romero N, Nicewicz D . Organic Photoredox Catalysis. Chem Rev. 2016; 116(17):10075-166. DOI: 10.1021/acs.chemrev.6b00057. View

Wang C, Lin P, Cheng C . Cobalt-catalyzed highly regio- and stereoselective intermolecular reductive coupling of alkynes with conjugated alkenes. J Am Chem Soc. 2002; 124(33):9696-7. DOI: 10.1021/ja026543l. View

Wu X, Zheng F . Synthesis of Carboxylic Acids and Esters from CO. Top Curr Chem (Cham). 2016; 375(1):4. DOI: 10.1007/s41061-016-0091-6. View

Takaya J, Iwasawa N . Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex. J Am Chem Soc. 2008; 130(46):15254-5. DOI: 10.1021/ja806677w. View

Huang K, Sun C, Shi Z . Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide. Chem Soc Rev. 2011; 40(5):2435-52. DOI: 10.1039/c0cs00129e. View

Takaya J, Sasano K, Iwasawa N . Efficient one-to-one coupling of easily available 1,3-dienes with carbon dioxide. Org Lett. 2011; 13(7):1698-701. DOI: 10.1021/ol2002094. View

10.

Qian X, Auffrant A, Felouat A, Gosmini C . Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates. Angew Chem Int Ed Engl. 2011; 50(44):10402-5. DOI: 10.1002/anie.201104390. View

11.

Fujihara T, Xu T, Semba K, Terao J, Tsuji Y . Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes. Angew Chem Int Ed Engl. 2010; 50(2):523-7. DOI: 10.1002/anie.201006292. View

12.

Murata K, Numasawa N, Shimomaki K, Takaya J, Iwasawa N . Construction of a visible light-driven hydrocarboxylation cycle of alkenes by the combined use of Rh(i) and photoredox catalysts. Chem Commun (Camb). 2017; 53(21):3098-3101. DOI: 10.1039/c7cc00678k. View

13.

Nogi K, Fujihara T, Terao J, Tsuji Y . Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO2. J Org Chem. 2015; 80(22):11618-23. DOI: 10.1021/acs.joc.5b02307. View

14.

Williams C, Johnson J, Rovis T . Nickel-catalyzed reductive carboxylation of styrenes using CO2. J Am Chem Soc. 2008; 130(45):14936-7. PMC: 2928647. DOI: 10.1021/ja8062925. View

15.

Leon T, Correa A, Martin R . Ni-catalyzed direct carboxylation of benzyl halides with CO2. J Am Chem Soc. 2013; 135(4):1221-4. DOI: 10.1021/ja311045f. View

16.

Wang S, Du G, Xi C . Copper-catalyzed carboxylation reactions using carbon dioxide. Org Biomol Chem. 2016; 14(15):3666-76. DOI: 10.1039/c6ob00199h. View

17.

Michigami K, Mita T, Sato Y . Cobalt-Catalyzed Allylic C(sp)-H Carboxylation with CO. J Am Chem Soc. 2017; 139(17):6094-6097. DOI: 10.1021/jacs.7b02775. View

18.

Hayashi T, Yamasaki K . Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions. Chem Rev. 2003; 103(8):2829-44. DOI: 10.1021/cr020022z. View

19.

Tsuji Y, Fujihara T . Carbon dioxide as a carbon source in organic transformation: carbon-carbon bond forming reactions by transition-metal catalysts. Chem Commun (Camb). 2012; 48(80):9956-64. DOI: 10.1039/c2cc33848c. View

20.

Shimomaki K, Murata K, Martin R, Iwasawa N . Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts. J Am Chem Soc. 2017; 139(28):9467-9470. DOI: 10.1021/jacs.7b04838. View