Welcome to visit The Chinese Journal of Process Engineering, Today is
Reviews

Advances on Hydroacylation Reaction Catalyzed by First-row Transition Metals

  • Ting LI Deping ZHU Baohua XU
Expand
  • 1. Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China; 2. School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China

Received date: 2017-03-17

  Revised date: 2017-03-31

  Online published: 2017-12-05

Abstract

Recently, the non-noble transition metals show an increasingly enormous application potential in homogeneous catalysis due to its relatively low cost and high abundance. And they are considered as promising catalysts which could serve as an alternative to the noble metals. The review summarizes the advances in hydroacylation, the addition of a formyl C?H bond across an unsaturated bond C X (X=C, O), catalyzed by first-row transition metals. And challenges focusing on scope of substrates, catalytic reactivity and selectivity, even the mechanism insight into the transformation are still worthy of exploration.

Cite this article

Ting LI Deping ZHU Baohua XU . Advances on Hydroacylation Reaction Catalyzed by First-row Transition Metals[J]. The Chinese Journal of Process Engineering, 2017 , 17(6) : 1127 -1133 . DOI: 10.12034/j.issn.1009-606X.217177

References

[1]Moselage M, Li J, Ackermann L.Cobalt-catalyzed C-H activation[J].ACS Catal, 2016, 6(2):498-525 [2]Gao K, Yoshikai N.Low-valent cobalt catalysis: new opportunities for C-H functionalization[J].Acc Chem Res, 2014, 47(4):1208-1219 [3]Gandeepan P, Cheng C H.Cobalt catalysis involving pi components in organic synthesis[J].Acc Chem Res, 2015, 48(4):1194-1206 [4]Li Y Y, Yu S L, Shen W Y, et, al.Iron-,cobalt-,and nickel-catalyzed asymmetric transfer hydrogenation and asymmetric hydrogenation of ketones[J].Acc Chem Res, 2015, 48(9):2587-2598 [5]Shibata Y, Tanaka K.Rhodium-catalyzed highly enantioselective direct intermolecular hydroacylation of 1,1-disubstituted alkenes with unfunctionalized aldehydes[J].J Am Chem Soc, 2009, 131(35):12552-12553 [6]Roy A H, Lenges C P, Brookhart M.Scope and mechanism of the intermolecular addition of aromatic aldehydes to olefins catalyzed by Rh(I) olefin complexes[J].J Am Chem Soc, 2007, 129(7):2082-2093 [7]Hyatt I F D, Anderson H K, Morehead A T, et, al.Mechanism of rhodium-catalyzed intramolecular hydroacylation: a computational study[J].Organometallics, 2008, 27(1):135-147 [8]Kundu K, McCullagh J V, Morehead A T.Hydroacylation of 2-vinyl benzaldehyde systems: an efficient method for the synthesis of chiral 3-substituted indanones[J].J Am Chem Soc, 2005, 127(46):16042-16043 [9]Kou K G M, Le D N, Dong V M.Rh(I)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides[J].J Am Chem Soc, 2014, 136(26):9471-9476 [10]Phan D H T, Kim B, Dong V M.Phthalides by rhodium-catalyzed ketone hydroacylation[J].J Am Chem Soc, 2009, 131(43):15608-15609 [11]Kim J, Yi C S.Intermolecular Markovnikov-selective hydroacylation of olefins catalyzed by a cationic ruthenium-hydride complex[J].ACS Catal, 2016, 6(5):3336-3339 [12] Omura S, Fukuyama T, Murakami Y, Okamoto H, Ryu I.Hydroruthenation triggered catalytic conversion of dialdehydes and keto aldehydes to lactones[J].Chem Chemmun, 2009, (44):6741-6743 [13]Suzuki T, Yamada T, Watanabe K, et, al.Iridium-catalyzed oxidative lactonization and intramolecular Tishchenko reaction of delta-ketoaldehydes for the synthesis of isocoumarins and 3,4-dihydroisocoumarins[J].Bioorg Med Chem Lett, 2005, 15(10):2583-2585 [14] Sakai K, Ide J, Oda O, et, al.Synthetic studies on prostanoids. 1. Synthesis of methyl 9-oxoprostanoate[J].Tetrahedron Lett, 1972, (13):1287-1290 [15] Coulter M M, Kou K G M, Galligan B, et, al.Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides[J].J Am Chem Soc, 2010, 132(46):16330-16333 [16] Coulter M M, Dornan P K, Dong V M.Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles[J].J Am Chem Soc, 2010, 131(20):6932-6933 [17]Jun C H, Moon C W, Lee D Y.Chelation-assisted carbon-hydrogen and carbon-carbon bond activation by transition metal catalysts [J].Chem Eur J, 2002, 8(11):2422-2428 [18] Khan H A, Kou K G M, Dong V M.Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones[J].Chem Sci, 2011, 2(3):407-410 [19] Willis M C, Randell-Sly H E, Woodward R L, et, al.Rhodium-catalyzed intermolecular chelation controlled alkene and alkyne hydroacylation: synthetic scope of β-S-substituted sldehyde substrates[J].J Org Chem, 2006, 71(14):5291-5297 [20] Coulter M M, Dornan P K, Dong V M.Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles[J].J Am Chem Soc, 2009, 131(20):6932-6933 [21]Lenges C P, Brookhart M.Co(I)-catalyzed inter- and intramolecular hydroacylation of olefins with aromatic aldehydes[J].J Am Chem Soc, 1997, 119(13):3165-3166 [22]Lenges C P, White P S, Brookhart M.Mechanistic and synthetic studies of the addition of alkyl aldehydes to vinylsilanes catalyzed by Co(I) complexes[J].J Am Chem Soc, 1998, 120(28):6965-6979 [23]Chen Q A, Kim D K, Dong V M.Regioselective hydroacylation of 1,3-dienes by cobalt catalysis[J].J Am Chem Soc, 2014, 136(10):3772-3775 [24]Santhoshkumar R, Mannathan S, Cheng C H.Ligand-controlled divergent C-H functionalization of aldehydes with enynes by cobalt catalysts[J].J Am Chem Soc, 2015, 137(51):16116-16120 [25]Yang J F, Yoshikai N.Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins[J].J Am Chem Soc, 2014, 136(48):16748-16751 [26]Yang J F, Seto Y W, Yoshikai N.Cobalt-catalyzed intermolecular hydroacylation of olefins through chelation-assisted imidoyl C-H activation[J].ACS Catal, 2015, 5(5):3054-3057 [27]Lenges C P, Brookhart M, White P S.Structure and reactivity of a cobalt(I) phthalaldehyde complex with both sigma- and pi-bonded aldehyde groups[J].Angew Chem Int Ed, 1999, 38(4):552-555 [28] Meng Q X, Wang F.Mechanisms and reactivity differences for the cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and alkenes: insights from density functional calculations [J].J Mol Model, 2016, 22(3):- [29]Tsuda T, Kiyoi T, Saegusa T.Nickel(0)-catalyzed hydroacylation of alkynes with aldehydes to α,β-enones[J].J Org Chem, 1990, 55(8):2554-2558 [30] Ogoshi S, Arai T, Ohashi M, et, al.Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde[J].Chem Commun, 2008, (11):1347-1349 [31]Hoshimoto Y, Hayashi Y, Suzuki H, et, al.Synthesis of five- and six-membered benzocyclic ketones through intramolecular alkene hydroacylation catalyzed by nickel(0)N-heterocyclic carbenes[J].Angew Chem Int Ed, 2012, 51(43):10812-10815 [32]Xiao L J, Fu X N, Zhou M J, et, al.Nickel-Catalyzed hydroacylation of styrenes with simple aldehydes: reaction development and mechanistic insights[J].J Am Chem Soc, 2016, 138(9):2957-2960 [33]Ogoshi H, Hoshimotoa Y, Ohashiab, M.Nickel-catalyzed Tishchenko reaction via hetero-nickelacycles by oxidative cyclization of aldehydes with nickel(0) complex[J].Chem Commun, 2010, 46(19):3354-3356 [34]Hoshimoto Y, Ohashi M, Ogoshi S.Nickel-Catalyzed Selective Conversion of Two Different Aldehydes to Cross-Coupled Esters[J].J Am Chem Soc, 2011, 133(13):4668-4671 [35]Doi R, Kikushima K, Ohashi M, et, al.Synthesis,Characterization,and Unique Catalytic Activities of a Fluorinated Nickel Enolate[J].J Am Chem Soc, 2015, 137(9):3276-3282 [36]Chen S F, Li X J, Zhao H Y, et, al.CuBr-promoted formal hydroacylation of 1-alkynes with glyoxal derivatives: an unexpected synthesis of 1,2-dicarbonyl-3-enes[J].J Org Chem, 2014, 79(9):4137-4141 [37]Yamamoto Y, Hayashi H, Saigoku T, et, al.Domino coupling relay approach to polycyclic pyrrole-2-carboxylates[J].J Am Chem Soc, 2005, 127(31):10804-10805 [38]Li J, Liu L, Ding D, Sun J T, et, al.Gold(III)-catalyzed three-component coupling reaction (TCC) selective toward furans[J].Org Lett, 2013, 15(11):2884-2887 [39] Shi S, Wang T, Weingand V, et, al.Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals[J].Angew Chem Int Ed, 2014, 53(4):1148-1151 [40] Bandar J S, Ascic E, Buchwald S L.Enantioselective CuH-catalyzed reductive coupling of aryl alkenes and activated carboxylic acids[J].J Am Chem Soc, 2016, 138(18):5821-5824 [41]Ohishi T, Shiotani Y, Yamashita M.Dimerization of Aromatic Aldehydes Catalyzed by K[CpFe(CO)2][J].Organometallics, 1994, 13(11):4641-4642 [42]Alvarez L X, Kudrik E V, Sorokin A B.Novel Reactivity of N-Bridged Diiron Phthalocyanine in the Activation of CH Bonds: Hydroacylation of Olefins as an Example of the Efficient Formation of CC Bonds[J].Chem Eur J, 2011, 17(34):9298-9301 [43]Ulrich D, Jankowski H.Investigations of properties of aluminum alcoholate catalyst used for the synthesis of ethyl-acetate from acetaldehyde[J].Chemische Technik, 1988, 40(9):393-397 [44]Hester A S, Himmler K.Chemicals from acetaldehyde[J].Industrial and Engineering Chemistry, 1959, 51(12):1424-1430 [45]Seki T, Nakajo T, Onaka Makoto.The Tishchenko reaction: A classic and practical tool for ester synthesis[J].Chemistry Letters, 2006, 35(8):824-829
Outlines

/