Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Topics in Current Chemistry

Volumn 374, Issue 4, 2016, Pages

  Juliá Hernández, Francisco ^a   Gaydou, Morgane ^a   Serrano, Eloisa ^a   van Gemmeren, Manuel ^a   Martin, Ruben ^a,b  

^a BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

Carboxylation; Carboxylic acids; Catalysis; CO2; Cross coupling; Iron; Nickel; Unsaturated hydrocarbons

Indexed keywords

EID: 84977144592     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/s41061-016-0045-z     Document Type: Review

References (129)

1. Aresta M (1999) Recovery and utilisation of carbon dioxide. RUCADI, EU Report
2. 2 capture and utilization: a tutorial review. Chem Soc Rev 43:7982–7994
3. 2 to chemicals, materials, and fuels. technological use of CO2. Chem Rev 114:1709–1742
4. 2 utilization by environmental-merit-order Curves. Environ Sci Technol 50:1093–1101
5. 2 Util 12:101–108
6. Mikkelsen M, Jørgensen M, Krebs FC (2010) The teraton challenge. A review of fixation and transformation of carbon dioxide. Energy Environ Sci 3:43–81
7. Wang S, Du G, Xi C (2016) Copper-catalyzed carboxylation reactions using carbon dioxide. Org Biomol Chem 14:3666–3676
8. Sekine K, Yamada T (2016) Silver-catalyzed carboxylation. Chem Soc Rev. doi:10.1039/c5cs00895f
9. 2. Coord Chem Rev 293–294:279–291
10. Guo C-X, Yu B, Ma R, He L-N (2015) Metal-promoted carboxylation of alkynes/allenes with carbon dioxide. Curr Green Chem 2:14–25
11. Industrial-scale preparation of low molecular weight acids is mainly carried out by carbonylation and/or oxidation of the corresponding alcohols and light olefins. See for instance: Samel U-R, Kohler W, Gamer A O, Keuser U, Yang S-T, Jin Y, Lin M, Wang Z (2014) Propionic acid and derivatives. Ullmann’s Encyclopedia of Industrial Chemistry 1–20
12. Correa A, Martin R (2009) Metal-catalyzed carboxylation of organometallic reagents with carbon dioxide. Angew Chem Int Ed 48:6201–6204
13. Brill M, Lazreg F, Cazin CSJ, Nolan SP (2016) Transition metal-catalyzed carboxylation of organic substrates with carbon dioxide. Top Organomet Chem 53:225–278
14. 2. J Am Chem Soc 136:1062–1069
15. 2. Angew Chem Int Ed 55:5053–5057
16. 2. J Am Chem Soc 137:6476–6479
17. 2 with C–C multiple bonds. Reaction mechanisms in carbon dioxide conversion: doi:10.1007/978-3-662-46831-9_5
18. Aresta M, Nobile CF, Albano VG, Forni E, Manassero M (1975) New nickel–carbon dioxide complex: synthesis, properties, and crystallographic characterization of (carbon dioxide)-bis(tricyclohexylphosphine)nickel. J Chem Soc Chem Commun. doi:10.1039/c39750000636
19. 2. Top Organomet Chem 53:39–71
20. 2 and epoxides: discovery, reactivity, optimization, and mechanism. Angew Chem Int Ed 43:6618–6639
21. Sa-A G, Sivaram S (1996) Organic carbonates. Chem Rev 96:951–976
22. Federsel C, Jackstell R, Beller M (2010) State-of-the-art catalysts for hydrogenation of carbon dioxide. Angew Chem Int Ed 49:6254–6257
23. Wang W, Wang S, Ma X, Gong J (2011) Recent advances in catalytic hydrogenation of carbon dioxide. Chem Soc Rev 40:3703–3727
24. Goeppert A, Czaun M, Jones JP, Surya Prakash GK, Olah GA (2014) Recycling of carbon dioxide to methanol and derived products—closing the loop. Chem Soc Rev 43:7995–8048
25. Matthessen R, Fransaer J, Binnemans K, De Vos DE (2014) Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids. Beilstein J Org Chem 10:2484–2500
26. Nogi K, Fujihara T, Terao J, Tsuji Y (2016) Carboxyzincation employing carbon dioxide and zinc powder: cobalt-catalyzed multicomponent coupling reactions with alkynes. J Am Chem Soc 138:5547–5550
27. Beller M, Gu X-F (2013) Transition metal catalyzed carbonylation reactions. Springer, New York
28. Fujihara T, Nogi K, Xu T, Terao J, Tsuji Y (2012) Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide. J Am Chem Soc 134:9106–9109
29. 2. J Am Chem Soc 136:11212–11215
30. Inoue Y, Itoh Y, Hashimoto H (1977) Incorporation of carbon dioxide in alkyne oligomerization catalyzed by nickel(0) complexes. Formation of substituted 2-pyrones. Chem Lett 6:855–856
31. Burkhart G, Hoberg H (1982) Oxanickelacyclopentene derivatives from Nickel(0), carbon dioxide, and alkynes. Angew Chem Int Ed 21:76
32. Sakaki S, Mine K, Taguchi D, Arai T (1993) Formation of the oxanickelacyclopentene complex from nickel(0), carbon dioxide, and alkyne. An ab initio MO/SD-CI study. Bull Chem Soc Jpn 66:3289–3299
33. Sakaki S, Mine K, Hamada T, Arai T (1995) Formation of the oxanickelacyclopentene complex from nickel(0), carbon dioxide, and alkyne. An ab initio MO/SD-CI Study. Part II. Reactivity and regioselectivity of hydroxyacetylene. Bull Chem Soc Jpn 68:1873–1882
34. Graham DC, Bruce MI, Metha GF, Bowie JH, Buntine MA (2008) Regioselective control of the nickel-mediated coupling of acetylene and carbon dioxide—a DFT study. J Organomet Chem 693:2703–2710
35. Li J, Jia G, Lin Z (2008) Theoritical studies on coupling reactions of carbon dioxide with alkynes mediated by Nickel(0) complexes. Organometallics 27:3892–3900
36. Saito S, Nakagawa S, Koizumi T, Hirayama K, Yamamoto Y (1999) Nickel-mediated regio- and chemoselective carboxylation of alkynes in the presence of carbon dioxide. J Org Chem 64:3975–3978
37. 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 36(22):2568–2569
38. Takimoto M, Shimizu K, Mori M (2001) Nickel-promoted alkylative or arylative carboxylation of alkynes. Org Lett 3:3345–3347
39. Shimizu K, Takimoto M, Mori M (2003) Novel synthesis of heterocycles having a functionalized carbon center via Nickel-mediated carboxylation: total synthesis of Erythrocarine. Org Lett 5:2323–2325
40. Shimizu K, Takimoto M, Sato Y, Mori M (2006) Total synthesis of (±)-erythrocarine using dienyne metathesis. J Organomet Chem 691:5466–5475
41. Saito N, Sun Z, Sato Y (2015) Nickel-promoted highly regioselective carboxylation of aryl ynol ether and its application to the synthesis of chiral beta-aryloxypropionic acid derivatives. Chem Asian J 10:1170–1176
42. 2 and novel cyclotrimerization. Chem Lett 7:633–634
43. Inoue Y, Itoh Y, Kazama H, Hashimoto H (1980) Reaction of dialkyl-substituted alkynes with carbon dioxide catalyzed by nickel(0) complexes. Incorporation of carbon dioxide in alkyne dimers and novel cyclotrimerization of the alkynes. Bull Chem Soc Jpn 53:3329–3333
44. Walther D, Schönberg H, Dinjus E (1987) Aktivierung von kohlendioxid an übergangsmetallzentren: selektive cooligomerisation mit hexin durch das katalysatorsystem acetonitril/trialkylphosphan/nickel(0) und struktur eines nickel(0)-komplexes mit side-on gebundenem acetonitril. J Org Chem 334:377–388
45. Tsuda T, Kunisada K, Nagahama N, Morikawa S, Saegusa T (1989) Nickel(0)-catalyzed cycloaddition of ethoxyethyne with carbon dioxide to 4,5-diethoxy-α-pyrone. Synth Commun 19:1575–1581
46. Tsuda T, Hasegawa N, Saegusa T (1990) Nickel(0)-catalysed novel co-oligomerization of ethoxy(trimethylsilyl)ethyne with carbon dioxide to 4,6-diethoxy-3-[1-ethoxy-2,2-bis(trimethylsilyl)vinyl]-5-(trimethylsilyl)-2-pyrone. J Chem Soc, Chem Commun 945–947
47. Hoberg H, Schaefer D, Burkhart G, Krüger C, Romao MJ (1984) Nickel(0)-induzierte C-C verknüpfung zwischen kohlendioxid und alkinen sowie alkenen. J Organomet Chem 266:203–224
48. Mori M (2007) Regio- and stereoselective synthesis of tri- and tetrasubstituted alkenes by introduction of CO2 and alkylzinc reagents into alkynes. Eur J Org Chem 2007:4981–4993
49. Shimizu K, Takimoto M, Sato Y, Mori M (2005) Nickel-catalyzed regioselective synthesis of tetrasubstituted alkene using alkylative carboxylation of disubstituted alkyne. Org Lett 7:195–197
50. Sato Y, Mori M, Shimizu K, Takimoto M (2006) Effective synthesis of tamoxifen using nickel-catalyzed arylative carboxylation. Synlett 2006:3182–3184
51. Buchwald SL, Nielsen RB (1989) Selective, zirconium-mediated cross-coupling of alkynes: synthesis of isomerically pure 1,3-dienes and 1,4-diiodo 1,3-dienes. J Am Chem Soc 111:2870–2874
52. Fujihara T, Horimoto Y, Mizoe T, Sayyed FB, Tani Y, Terao J, Sakaki S, Tsuji Y (2014) Nickel-catalyzed double carboxylation of alkynes employing carbon dioxide. Org Lett 16:4960–4963
53. Li S, Yuan W, Ma S (2011) Highly regio- and stereoselective three-component nickel-catalyzed syn-hydrocarboxylation of alkynes with diethyl zinc and carbon dioxide. Angew Chem Int Ed 50:2578–2582
54. Fujihara T, Xu T, Semba K, Terao J, Tsuji Y (2011) Copper-catalyzed hydrocarboxylation of alkynes using carbon dioxide and hydrosilanes. Angew Chem Int Ed 50:523–527
55. Li S, Ma S (2011) Highly selective nickel-catalyzed methyl-carboxylation of homopropargylic alcohols for α-alkylidene-γ-butyrolactones. Org Lett 13:6046–6049
56. 2-activation for gamma-butyrolactones and its application in the total synthesis of (±)-heteroplexisolide E. Chem Asian J 7:2411–2418
57. Wang X, Nakajima M, Martin R (2015) Ni-catalyzed regioselective hydrocarboxylation of alkynes with CO2 by using simple alcohols as proton sources. J Am Chem Soc 137:8924–8927
58. Trost BM, Ball ZT (2005) Addition of metalloid hydrides to alkynes: hydrometallation with Boron, Silicon, and Tin. Synthesis 6:853–887
59. Fu M-C, Shang R, Cheng W-M, Fu Y (2016) Nickel-catalyzed regio- and stereoselective hydrocarboxylation of alkynes with formic acid through catalytic CO recycling. ACS Catal 6:2501–2505
60. Hoberg H, Schaefer D (1982) Nickel(0)-induzierte C-C verknupfung zwischen alkenen und kohlendioxid. J Organomet Chem 236:C28–C30
61. Hoberg H, Schaefer D (1983) Nickel(0)-induzierte C-C verknupfung zwischen kohlendioxid und etylen sowie mono- oder di-substituierten alkenen. J Organomet Chem 1983:C51–C53
62. Hoberg H, Peres Y, Milchereit A (1986) C-C Verknupfung von alkenen mit CO2 an Nickel(0); Herstellung von zimtsaure aus styrol. J Organomet Chem 307:C38–C40
63. Hoberg H, Ballesteros A, Sigan A, Jegat C, Barhausen D, Milchereit A (1991) Ligandgesteuerte ringkontraktion von Nickela-funfin vierringkomplexe-neuartige startsysteme fur die praparative Chemie. J Organomet Chem 407:C23–C29
64. 2 to anhydrides and ketoacids. Dalton Trans 43:15990–15996
65. Murakami M, Ishida N, Miura T (2006) Solvent and ligand partition reaction pathways in nickel-mediated carboxylation of methylenecyclopropanes. Chem Comm 14(6):643–645
66. Guo C-H, Tian L-C, Jia J, Wu H-S (2014) Theoretical study on the nickel(0)-mediated coupling of carbon dioxide and benzylidenecyclopropane: mechanism and selectivity. Comput Theor Chem 1044:44–54
67. Aresta M, Quaranta E, Tommasi I (1988) Reduction of coordinated carbon dioxide to carbon monoxide via protonation by thiols and other Bronsted acids by Ni-systems: a contribution to the understanding of the mode of action of the enzyme carbon monoxide dehydrogenase. J Chem Soc, Chem Commun. doi:10.1039/c39880000450
68. 2 to a metal center. Inorg Chem 31:4286–4290
69. 2 with C2H4. Organometallics 23:5252–5259
70. Yang G, Schäffner B, Blug M, Hensen EJM, Pidko EA (2014) A mechanistic study of Ni-catalyzed carbon dioxide coupling with ethylene towards the manufacture of acrylic acid. Chem Cat Chem 6:800–807
71. Plessow PN, Schäfer A, Limbach M, Hofmann P (2014) Acrylate formation from CO2 and ethylene mediated by Nickel complexes: a theoretical study. Organometallics 33:3657–3668
72. Hoberg H, Peres Y, Kruger C, Tsay Y-H (1987) A 1-oxa-2-nickela-5-cyclopentanone from ethene and carbon dioxide: preparation, structure, and reactivity. Angew Chem Int Ed 26:771–773
73. Hoberg H, Jenni K, Angermund K, Kruger C (1987) C-C-Linkages of ethene with CO2 on an Iron(0) complex - Synthesis and crystal structure analysis of [(PEt3)2Fe(C2H4)2]. Angew Chem Int Ed 26:153–155
74. Kirillov E, Carpentier JF, Bunel E (2015) Carboxylic acid derivatives via catalytic carboxylation of unsaturated hydrocarbons: whether the nature of a reductant may determine the mechanism of CO2 incorporation? Dalton Trans 44:16212–16223
75. Lapidus AL, Pirozhkov SD, Koryakin AA (1978) Catalytic synthesis of propionic acid by carboxylation of ethylene with carbon dioxide. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 12:2814–2816
76. Williams CM, Johnson JB, Rovis T (2008) Nickel-catalyzed reductive carboxylation of styrenes using CO2. J Am Chem Soc 130:14936–14937
77. Yuan R, Lin Z (2014) Computational insight into the mechanism of Nickel-catalyzed reductive carboxylation of styrenes using CO2. Organometallics 33:7147–7156
78. Shirakawa E, Ikeda D, Masui S, Yoshida M, Hayashi T (2012) Iron-copper cooperative catalysis in the reactions of alkyl Grignard reagents: exchange reaction with alkenes and carbometalation of alkynes. J Am Chem Soc 134:272–279
79. Greenhalgh MD, Thomas SP (2012) Iron-catalyzed, highly regioselective synthesis of alpha-aryl carboxylic acids from styrene derivatives and CO2. J Am Chem Soc 134:11900–11903
80. Rio I, Claver C, van Leeuwen PWNM (2001) On the mechanism of the hydroxycarbonylation of styrene with palladium systems. Eur J Inorg Chem 2001:2719–2738
81. Smith BRJ, Loganathan M, Shantha MS (2010) A review of the water gas shift reaction kinetics. Int J Chem React Eng 8:1542
82. Ostapowicz TG, Schmitz M, Krystof M, Klankermayer J, Leitner W (2013) Carbon dioxide as a C(1) building block for the formation of carboxylic acids by formal catalytic hydrocarboxylation. Angew Chem Int Ed 52:12119–12123
83. González-Sebastián L, Flores-Alamo M, García JJ (2012) Nickel-catalyzed reductive hydroesterification of styrenes using CO2 and MeOH. Organometallics 31:8200–8207
84. Wu L, Liu Q, Fleischer I, Jackstell R, Beller M (2014) Ruthenium-catalysed alkoxycarbonylation of alkenes with carbon dioxide. Nat Commun 5:3091
85. 2 Util 1:60–68
86. Limbach M (2015) Acrylates from alkenes and CO2, the stuff that dreams are made of. Adv Organomet Chem 63:175–202
87. Graham DC, Mitchell C, Bruce MI, Metha GF, Bowie JH, Buntine MA (2007) Production of acrylic acid through Nickel-mediated coupling of ethylene and carbon dioxide—a DFT Study. Organometallics 26:6784–6792
88. 2 and ethylene: the transformation of a nickelalactone into a nickel-acrylate complex. Chem Comm 2510–2512
89. 2 and ethylene via methylation of nickelalactones. Organometallics 29:2199–2202
90. Lee SY, Cokoja M, Drees M, Li Y, Mink J, Herrmann WA, Kuhn FE (2011) Transformation of nickelalactones to methyl acrylate: on the way to a catalytic conversion of carbon dioxide. Chem Sus Chem 4:1275–1279
91. Lee SYT, Ghani AA, D’Elia V, Cokoja M, Herrmann WA, Basset J-M, Kühn FE (2013) Liberation of methyl acrylate from metallalactone complexes via M–O ring opening (M=Ni, Pd) with methylation agents. New J Chem 37:3512
92. 2, ethylene and methyl iodide. Organometallics 32:3327–3338
93. 2 and ethylene. Organometallics 32:2152–2159
94. 2 on Ni complexes: a mechanistic viewpoint from a hybrid DFT approach. Organometallics 33:6369–6380
95. 2-ethylene coupling to acrylates. Chem Eur J 20:3205–3211
96. 2 and an alkene-a rational approach. Chem Eur J 18:14017–14025
97. 2 using sodium alkoxides as bases. Catal Today. doi:10.1016/j.cattod.2016.03.025
98. 2: one-pot synthesis of alpha, beta-unsaturated carboxylic acid salts. Chem Eur J 20:16858–16862
99. 2 towards alpha, beta-unsaturated carboxylic acid salts: characterization of intermediates and ligands as well as substrate effects. Dalton Trans 44:11083–11094
100. Hendriksen C, Pidko EA, Yang G, Schaffner B, Vogt D (2014) Catalytic formation of acrylate from carbon dioxide and ethene. Chem Eur J 20:12037–12040
101. 2, and phenolate bases: optimization of the catalytic system for a potential process. Eur J Org Chem 2015:7122–7130
102. Goossen LJ, Goossen K (2008) Nachhaltigkeit durch atomökonomische Synthesen. Aktuelle Wochenschau der GDCh:18
103. Hoberg H, Oster BW (1984) Nickel(0)-induzierte C–C-verknüpfung zwischen 1,2-dienen und kohlendioxid. J Organomet Chem 266:321–326
104. Takimoto M, Kawamura M, Mori M (2003) Nickel(0)-mediated sequential addition of carbon dioxide and aryl aldehydes into terminal allenes. Org Lett 5:2599–2601
105. Takimoto M, Kawamura M, Mori M (2004) Nickel-mediated regio- and stereoselective carboxylation of trimethylsilylallene under an atmosphere of carbon dioxide. Synthesis 2004:791–795
106. 2. Synlett 2011:1423–1426
107. 2 and O2. Org Lett 9:1251–1253
108. Dérien S, Clinet J-C, Duñach E, Périchon J (1990) Coupling of allenes and carbon dioxide catalyzed by electrogenerated nickel complexes. Synlett 2:361–364
109. Takimoto M, Kawamura M, Mori M, Sato Y (2005) Nickel-catalyzed regio- and stereoselective double carboxylation of trimethylsilylallene under an atmosphere of carbon dioxide and its application to the synthesis of Chaetomellic acid A anhydride. Synlett 2005:2019–2022
110. Walther D, Dinjus E (1982) Aktivierung von Kohlendioxid an Übergangsmetallzentren; Die Metallaringschlußreaktion zwischen Kohlendioxid und 1,3-Dienen am elektronenreichen Nickel (0)-Komplexrumpf. Zeitschrift für Chemie 22:228–229
111. 2 an übergangsmetallzentren: struktur and reaktivität eines C–C-kopplungsproduktes von CO2 und 2.3-dimethylbutadien am elektronenreichen Nickel(0). Z Naturforsch B 38:835–840
112. Hoberg H, Apotecher B (1984) α, ω-Disäuren aus butadien und kohlendioxid an nickel(0). J Organomet Chem 270:c15–c17
113. 2 durch C–C-verknüpfung an nickel(0). J Organomet Chem 266:313–320
114. 2 durch C–C-Verknüpfung an nickel(0). J Organomet Chem 255:C15–C17
115. Behr A, Kanne U (1986) Nickel complex induced C–C-linkage of carbon dioxide with trienes. J Organomet Chem 317:C41–C44
116. 2 und Butadien an Eisen(o)-Komplexen—ein neuer Weg zu α, ω-Dicarbonsäuren. Angew Chem 98:819–820
117. Geyer C, Schindler S (1998) Kinetic analysis of the reaction of isoprene with carbon dioxide and a Nickel(0) complex. Organometallics 17:4400–4405
118. Takimoto M, Mori M (2001) Cross-coupling reaction of oxo–allylnickel complex generated from 1,3-diene under an atmosphere of carbon dioxide. J Am Chem Soc 123:2895–2896
119. Takimoto M, Mizuno T, Sato Y, Mori M (2005) Nickel-mediated carboxylative cyclization of enynes. Tetrahedron Lett 46:5173–5176
120. Takimoto M, Mizuno T, Mori M, Sato Y (2006) Nickel-mediated cyclization of enynes under an atmosphere of carbon dioxide. Tetrahedron 62:7589–7597
121. Mizuno T, Oonishi Y, Takimoto M, Sato Y (2011) Total synthesis of (–)-Corynantheidine by Nickel-catalyzed carboxylative cyclization of enynes. Eur J Org Chem 2011:2606–2609
122. 2. Angew Chem Int Ed 26:571–572
123. Tsuda T, Morikawa S, Sumiya R, Saegusa T (1988) Nickel(0)-catalyzed cycloaddition of diynes and carbon dioxide to give bicyclic α-pyrones. J Org Chem 53:3140–3145
124. Tsuda T, Morikawa S, Hasegawa N, Saegusa T (1990) Nickel(0)-catalyzed cycloaddition of silyl diynes with carbon dioxide to silyl bicyclic α-pyrones. J Org Chem 55:2978–2981
125. Tekavec TN, Arif AM, Louie J (2004) Regioselectivity in nickel(0) catalyzed cycloadditions of carbon dioxide with diynes. Tetrahedron 60:7431–7437
126. 2 and diynes. J Am Chem Soc 124:15188–15189
127. Cao T, Ma S (2016) Highly stereo- and regioselective hydrocarboxylation of diynes with carbon dioxide. Org Lett 18:1510–1513
128. 2 incorporation reaction: nickel-catalyzed regio- and stereoselective ring-closing carboxylation of bis-1,3-dienes. J Am Chem Soc 124:10008–10009
129. 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