Copper- and copper-N-heterocyclic carbene-catalyzed C-H activating carboxylation of terminal alkynes with CO2 at ambient conditions

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 47, 2010, Pages 20184-20189

  Yu, Dingyi ^a   Zhang, Yugen ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBENE; CARBON; CARBON DIOXIDE; COPPER; HYDROGEN;

CARBOXYLATION; CATALYSIS; CONFERENCE PAPER; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 78650551466     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1010962107     Document Type: Article

References (48)

1. Marks TJ, et al. (2001) Catalysis research of relevance to carbon management: Progress, challenges, and opportunities. Chem Rev 101:953-996.
2. Sakakura T, Choi JC, Yasuda H (2007) Transformation of carbon dioxide. Chem Rev 107:2365-2387.
3. 2. Chem Rev 107:2388-2410.
4. Eghbali N, Li C-J (2007) Conversion of carbon dioxide and olefins into cyclic carbonates in water. Green Chem 9:213-215.
5. Riduan SN, Zhang Y, Ying JY (2009) Conversion of carbon dioxide to methanol with silanes over N-heterocyclic carbene catalysts. Angew Chem, Int Ed 48:3322-3325.
6. Sakakura T, Kohon K (2009) The synthesis of organic carbonates from carbon dioxide. Chem Commun 1312-1330.
7. 2 splitting reactions to form CO with N-heterocyclic carbenes as organocatalysts and aromatic aldehydes as oxygen acceptors. J Am Chem Soc 132:914-915.
8. 2 in carbonates: Routes to valuable products and long-term storage. Catal Today 115:73-79.
9. Aresta M, Dibenedetto A, Tommasi I (2001) Developing innovative synthetic technologies of industrial relevance based on carbon dioxide as raw material. Energy Fuels 15:269-273.
10. Tundo P, Selva M (2002) The chemistry of dimethyl carbonate. Acc Chem Res 35:706-716.
11. Olah GA (2005) Beyond oil and gas: The methanol economy. Angew Chem, Int Ed 44:2636-2639.
12. Aida T, Inoue S (1996) Metalloporphyrins as initiators for living and immortal polymerizations. Acc Chem Res 29:39-48. (Pubitemid 126468522)
13. Riduan SN, Zhang Y (2010) Recent developments in carbon dioxide utilization under mild conditions. Dalton Trans 39:3347-3357.
14. Kubota T, et al. (2001) Kinetic study of methanol synthesis from carbon dioxide and hydrogen. Appl Organomet Chem 15:121-126.
15. Omae I (2006) Aspects of carbon dioxide utilization. Catal Today 115:33-52.
16. Correa A, Martin R (2009) Metal-catalyzed carboxylation of organometallic reagents with carbon dioxide. Angew Chem, Int Ed 48:6201-6204.
17. Bew SP (2005) ComprehensiveOrganic Functional Groups Transformation II, eds AR Katritzky and RJK Taylor (Elsevier, Oxford) p 19.
18. Ebert GW, et al. (2005) Carboxylation and esterification of functionalized arylcopper reagents. J Org Chem 70:4314-4317.
19. Olah GA, et al. (2002) Efficient chemoselective carboxylation of aromatics to arylcarboxylic acids with a superelectrophilically activated carbon dioxide-Al2Cl6/Al system. J Am Chem Soc 124:11379-11391.
20. Shi M, Nicholas KM (1997) Palladium-catalyzed carboxylation of allyl stannanes. J Am Chem Soc 119:5057-5058.
21. 2. J Am Chem Soc 130:7826-7827.
22. 2. Org Lett 10:2681-2683.
23. 2 in DMF solvent. Org Lett 11:2035-2037.
24. 2. J Am Chem Soc 128:8706-8707.
25. Ohishi T, Nishiura M, Hou Z (2008) CuCl-NHC-catalyzed carboxylation of aryl- and alkenylboronic esters. Angew Chem, Int Ed 47:5792-5795.
26. Takaya Jun, Tadami Satoshi, Ukai Kazutoshi, Iwasawa Nobuharu (2008) Copper(I)- catalyzed carboxylation of aryl- and alkenylboronic esters. Org Lett 10:2697-2700.
27. Aoki M, Kaneko M, Izumi S, Ukai K, Iwasawa N (2004) Bidentate amidine ligands for nickel(0)-mediated coupling of carbon dioxide with unsaturated hydrocarbons. Chem Commun 2568-2569.
28. 2 and diynes. J Am Chem Soc 124:15188-15189.
29. Takimoto M, Nakamura Y, Kimura K, Mori M (2004) Highly enantioselective catalytic carbon dioxide incorporation reaction: Nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes. J Am Chem Soc 126:5956-5957.
30. 2. J Am Chem Soc 130:14936-14937.
31. 2 catalyzed by silyl pincer-type palladium complex. J Am Chem Soc 130:15254-15255.
32. Boogaerts Ine IF, Nolan Steven P (2010) Carboxylation of C-H bonds using N-heterocyclic carbene gold(I) complexes. J Am Chem Soc 132:8858-8859.
33. Bonne D, Dekhane M, Zhu J (2007) Fibrous aggregation of magnetite nanoparticles induced by a time-varied magnetic field. Angew Chem, Int Ed 46:2485-2488.
34. Lehmann F, et al. (2007) Design, parallel synthesis and SAR of novel urotensin II receptor agonists. Eur J Med Chem 42:276-285.
35. Nagata W, Yoshioka M (1977) Hydrocyanation of conjugated carbonyl compounds. Org React 25:255-476.
36. Deutsch C, Krause N (2008) CuH-catalyzed reactions. Chem Rev 108:2916-2927.
37. Evano G, Blanchard N, Toumi M (2008) Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. Chem Rev 108:3054-3131.
38. Shibasaki M, Kanai M (2008) Catalytic enantioselective cyanosilylation of ketones. Chem Rev 108:2853-2873.
39. Hay AS (1962) Oxidative coupling of acetylenes. II. J Org Chem 27:3320-3321.
40. 2, and bromoalkanes catalysed by copper(I) or silver(I) salt. Chem Commun 2091.
41. Tetsuo T, Kazuo U, Takeo S (1974) Carbon dioxide insertion into organocopper and organosilver compounds. Chem Commun 380-381.
42. Vechorkin O, Hirt N, Hu X (2010) Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles. Org Lett 12:3567-3569.
43. Barnea E, Eisen MS (2006) Organoactinides in catalysis. Coord Chem Rev 250:855-899.
44. Park EJ, Kim SH, Chang S (2008) Copper-catalyzed reaction of a-aryldiazoesters with terminal alkynes: A formal [3 + 2] cycloaddition route leading to indene derivatives. J Am Chem Soc 130:17268-17269.
45. Zhang Y, Ngeow K, Ying JY (2007) The first N-heterocyclic carbene (NHC)-based nickel catalyst for C-S coupling. Org Lett 9:3495-3499.
46. Zhang Y, Zhao L, Patra PK, Hu D, Ying JY (2009) Colloidal poly-imidazolium salts and derivatives. Nano Today 4:13-20.
47. Tan MX, Zhang Y, Ying JY (2009) Hydrosilylation of ketone and imine over poly-Nheterocyclic carbene particles. Adv Synth Catal 351:1390-1394.
48. Adimurthy S, Malakar CC, Beifuss U (2009) Influence of bases and ligands on the outcome of the Cu(I)-catalyzed oxidative homocoupling of terminal alkynes to 1,4-disubstituted 1,3-diynes using oxygen as an oxidant. J Org Chem 74:5648-5651.