Mechanisms and reactivity differences for the cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and alkenes: insights from density functional calculations

详细信息    查看全文

• 作者：Qingxi Meng ; Fen Wang
• 关键词：Cobalt ; Hydroacylation ; Ketone ; Alkene ; DFT
• 刊名：Journal of Molecular Modeling
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：22
• 期：3
• 全文大小：1,699 KB
• 参考文献：1.Murphy SK, Park J, Cruz FA, Dong VM (2015) Rh-catalyzed C–C bond cleavage by transfer hydroformylation. Science 347:56–60
  2.Henrion M, Ritleng V, Chetcuti MJ (2015) Nickel N-heterocyclic carbene-catalyzed C–C bond formation: reactions and mechanistic aspects. ACS Catal 5:1283–1302
  3.Sipos G, Drinkel EE, Dorta R (2015) The emergence of sulfoxides as efficient ligands in transition metal catalysis. Chem Soc Rev 44:3834–3860CrossRef
  4.Arockiam PB, Bruneau C, Dixneuf PH (2012) Ruthenium(II)-catalyzed C–H bond activation and functionalization. Chem Rev 112:5879–5918
  5.Ackermann L (2011) Carboxylate-assisted transition-metal-catalyzed C–H bond functionalizations: mechanism and scope. Chem Rev 111:1315–1345
  6.Balcells D, Clot E, Eisenstein O (2010) C–H bond activation in transition metal species from a computational perspective. Chem Rev 110:749–823
  7.Liu B, Hu F, Shi BF (2015) Recent advances on ester synthesis via transition-metal catalyzed C–H functionalization. ACS Catal 5:1863–1881
  8.Murphy SK, Dong VM (2014) Enantioselective hydroacylation of olefins with rhodium catalysis. Chem Commun 50:13645–13649CrossRef
  9.Leung JC, Krische M (2012) Catalytic intermolecular hydroacylation of C–C π-bonds in the absence of chelation assistance. Chem Sci 3:2202–2209
  10.Willis MC (2010) Transition metal catalyzed alkene and alkyne hydroacylation. Chem Rev 110:725–748CrossRef
  11.Jun CH, Jo EA, Park JW (2007) Intermolecular hydroacylation by transition-metal complexes. Eur J Org Chem 1869–1881
  12.Frost BM (2002) On inventing reactions for atom economy. Acc Chem Res 35:695–705CrossRef
  13.Vinogradov MG, Tuzikov AB, Nikishin GI (1985) Intramolecular hydroacylation catalyzed by cobalt complexes. Russ Chem Bull 34:325–329CrossRef
  14.Vinogradov MG, Tuzikov AB, Nikishin GI (1985) Intramolecular hydroacylation reaction catalyzed by Co2(N2)(PPh3)6 in the presence of various ligands. Russ Chem Bull 34:2369–2374
  15.Vinogradov MG, Tuzikov AB, Nikishin GI (1989) Cyclization of unsaturated aldehydes catalyzed by (PPh3)2Co(L2). Russ Chem Bull 38:2353–2356CrossRef
  16.Vinogradov MG, Tuzikov AB, Nikishin GI, Shelimov BN, Kazansky VB (1988) Unusual type of catalysis by paramagnetic cobalt(0) complexes. Isolation of catalytically active 17-electron intermediate, (Ph3P)2Co(CH2=CHCH2CH2CHO), in the 4-pentenal intramolecular hydroacylation. J Organomet Chem 348:123–134CrossRef
  17.Lenges CP, White PS, Brookhart M (1998) Mechanistic and synthetic studies of the addition of alkyl aldehydes to vinylsilanes catalyzed by Co(I) complexes. J Am Chem Soc 120:6965–6975CrossRef
  18.Chen QA, Kim DK, Dong VM (2014) Regioselective hydroacylation of 1,3-dienes by cobalt catalysis. J Am Chem Soc 136:3772–3775CrossRef
  19.Yang J, Yoshikai N (2014) Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins. J Am Chem Soc 136:16748–16751CrossRef
  20.Yang J, Yuan WS, Yoshikai N (2015) Cobalt-catalyzed intermolecular hydroacylation of olefins through chelation-assisted imidoyl C–H activation. ACS Catal 5:3054–3057
  21.Hoshimoto Y, Ohashi M, Ogoshi S (2015) Catalytic transformation of aldehydes with nickel complexes through η2 coordination and oxidative cyclization. Acc Chem Res 48:1746–1755CrossRef
  22.Hoshimoto Y, Hayashi Y, Suzuki H, Ohashi M, Ogoshi S (2012) Synthesis of five- and six-membered benzocyclic ketones through intramolecular alkene hydroacylation catalyzed by nickel(0)/N-heteracyclic carbenes. Angew Chem Int Ed 51:10812–10815CrossRef
  23.Taniguchi H, Ohmura T, Suginome M (2009) Nickel-catalyzed ring-opening hydroacylation of methylenecyclopropanes: synthesis of γ,δ-unsaturated ketones from aldehydes. J Am Chem Soc 131:11298–11299
  24.Chen S, Li X, Zhao H, Li B (2014) CuBr-promoted formal hydroacylation of 1-alkynes with glyoxal derivatives: an unexpected synthesis of 1,2-dicarbonyl-3-enes. J Org Chem 79:4137–4141CrossRef
  25.Qin Y, Peng Q, Song J, Zhou D (2011) Highly efficient copper-catalyzed hydroacylation reaction of aldehydes with azodicarboxylates. Tetrahedron Lett 52:5880–5883CrossRef
  26.Omura S, Fukuyama T, Horiguchi J, Murakami Y, Ryu I (2008) Ruthenium hydride-catalyzed addition of aldehydes to dienes leading to β,γ-unsaturated ketones. J Am Chem Soc 130:14094–14095
  27.Shibahara F, Bower JF, Krische MJ (2008) Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C–C bond-forming transfer hydroacylation: synthesis of β,γ-unsaturated ketones. J Am Chem Soc 130:14120–14122
  28.Miura H, Wada K, Hosokawa S, Inoue M (2013) Ruthenium-catalyzed intermolecular hydroacylation of internal alkynes: the use of ceria-supported catalyst facilitates the catalyst recycling. Chem Eur J 19:861–864
  29.Murphy SK, Dong VM (2013) Enantioselective ketone hydroacylation using Noyori’s transfer hydrogenation catalyst. J Am Chem Soc 135:5553–5556CrossRef
  30.Chen Q, Cruz FA, Dong VM (2015) Alkyne hydroacylation: switching regioselectivity by tandem ruthenium catalysis. J Am Chem Soc 137:3157–3160
  31.Murphy SK, Bruch A, Dong VM (2015) Mechanistic insights into hydroacylation with non-chelating aldehydes. Chem Sci 6:174–180CrossRef
  32.Kou KGM, Le DN, Dong VM (2014) Rh(I)-catalyzed intermolecular hydroacylation: enantioselective cross-coupling of aldehydes and ketoamides. J Am Chem Soc 136:9471–9476CrossRef
  33.Souillart L, Cramer N (2014) Highly enantioselective rhodium(I)-catalyzed carbonyl carboacylations initiated by C–C bond activation. Angew Chem Int Ed 53:9640–9644
  34.Murphy SK, Bruch A, Dong VM (2014) Substrate-directed hydroacylation: rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes. Angew Chem Int Ed 53:2455–2459
  35.Du X, Ghosh A, Stanley LM (2014) Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance. Org Lett 16:4036–4039CrossRef
  36.Ghosh A, Stanley LM (2014) Enantioselective hydroacylation of N-vinylindole-2-carboxaldehydes. Chem Commun 50:2765–2768
  37.Zhang T, Qi Z, Zhang X, Wu L, Li X (2014) RhIII-catalyzed hydoacylation reactions between N-sulfonyl 2-aminobenzaldehydes and olefins. Chem Eur J 20:3283–3288
  38.Castaing M, Wason SL, Estepa B, Hooper JF, Willis MC (2013) 2-Aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: application to dihydoquinolone synthesis. Angew Chem Int Ed 52:13280–13283
  39.Jijy E, Prakash P, Shimi M, Pihko PM, Josepha N, Radhakrishnan KV (2013) Rhodium catalyzed oxidative coupling of salicylaldehydes with diazabicyclic olefins: a one pot strategy involving aldehyde C–H cleavage and π-allyl chemistry towards the synthesis of fused ring chromanone. Chem Commun 49:7349–7351CrossRef
  40.Fujihara T, Tatsumi K, Terao J, Tsujis Y (2013) Palladium-catalyzed formal hydroacylation of allenes employing acid chlorides and hydrosilanes. Org Lett 15:2286–2289CrossRef
  41.Fujihara T, Hosomi T, Cong C, Hosoki T, Terao J, Tsuji Y (2015) Palladium-catalyzed formal hydroacylation of allenes employing carboxylic anhydrides and hydrosilanes. Tetrahedron 71:4570–4574CrossRef
  42.Hatanaka S, Obora Y, Ishii Y (2010) Iridium-catalyzed coupling reaction of primary alcohols with 2-alkynes leading hydroacylation products. Chem Eur J 16:1883–1888CrossRef
  43.Shi S, Wang T, Weingand V, Rudolph M, Hashmi ASK (2014) Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals. Angew Chem Int Ed 53:1148–1151CrossRef
  44.Meng QX, Wang F, Li M (2013) Theoretical investigation of Co(0)-catalyzed intramolecular hydroacylation of 4-pentenal. J Mol Model 19:2225–2234
  45.Meng QX, Wang F, Yin HZ (2015) Theoretical studies of cobalt(I)-catalyzed hydroacylation of vinylsilanes and alkyl aldehydes. J Phys Org Chem 28:431–436CrossRef
  46.Hyatt IFD, Anderson HK, Morehead AT Jr, Sargent AL (2008) Mechanism of rhodium-catalyzed intramolecular hydroacylation: a computational study. Organometallics 27:135–147CrossRef
  47.Chung LW, Wiest O, Wu YD (2008) A theoretical study on the trans-addition intramolecular hydroacylation of 4-alkynals catalyzed by cationic rhodium complexes. J Org Chem 73:2649–2655
  48.Meng QX, Shen W, Li M (2012) Mechanism of intermolecular hydroacylation of vinylsilanes catalyzed by rhodium(I) olefin complex: a DFT study. J Mol Model 18:1229–1239
  49.Wang F, Meng QX, Li M (2014) Theoretical studies of ruthenium hydride-catalyzed addition reactions of benzaldehydes to isoprenes leading to β,γ-unsaturated ketones: the role of the ligands hydride, carbonyl, chloride, and triphenylphosphine of the catalyst. J Organomet Chem 753:1–8
  50.Meng QX, Wang F, Li M (2012) Ruthenium hydride-catalyzed regioselective addition of benzaldehyde to dienes leading to β,γ-unsaturated ketones: a DFT study. J Mol Model 18:4955–4963
  51.Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JAJ, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, revision C.01. Gaussian, Inc., Wallingford
  52.Parr RG, Yang W (1989) Density-functional theory of atoms and molecules. Oxford University Press, New York
  53.Zhao Y, Truhlar DG (2008) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Acc 120:215–241
  54.Rassolov VA, Ratner MA, Pople JA, Redfern PC, Curtiss LA (2001) 6-31G* basis set for third-row atoms. J Comput Chem 22:976–984CrossRef
  55.Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J (1988) A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements. J Chem Phys 89:2193–2218CrossRef
  56.Heher WJ, Ditchfield R, Pople JA (1972) Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257–2261CrossRef
  57.Hay PJ, Wadt WR (1985) Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals. J Chem Phys 82:299–310CrossRef
  58.Wadt WR, Hay PJ (1985) Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi. J Chem Phys 82:284–298CrossRef
  59.Hay PJ, Wadt WR (1985) Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg. J Chem Phys 82:270–283CrossRef
  60.Ehlers AW, Böhme M, Dapprich S, Gobbi A, Höllwarth A, Jonas V, Köhler KF, Stegmann R, Veldkamp A, Frenking G (1993) A set of f-polarization functions for pseudo-potential basis sets of the transition metals Sc–Cu, Y–Ag and La–Au. Chem Phys Lett 208:111–114
  61.Gonzalez C, Schlegel HB (1990) Reaction path following in mass-weighted internal coordinates. J Phys Chem 94:5523–5527CrossRef
  62.Carpenter JE, Weinhold F (1988) Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure. J Mol Struct THEOCHEM 169:41–50
  63.Foster JP, Weinhold F (1980) Natural hybrid orbitals. J Am Chem Soc 102:7211–7218CrossRef
  64.Reed AE, Weinstock RB, Weinhold F (1985) Natural population analysis. J Chem Phy 83:735–746CrossRef
  65.Reed AE, Curtiss LA, Weinhold F (1988) Intermolecular interactions from a natural bond orbital, donor–acceptor viewpoint. Chem Rev 88:899–926
  66.Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F (2001) NBO 5.0. Theoretical Chemistry Institute, University of Wisconsin, Madison
  67.Gandeepan P, Cheng CH (2015) Cobalt catalysis involving π components in organic synthesis. Acc Chem Res 48:1194–1206CrossRef
  68.Santhoshkumar R, Mannathan S, Cheng CH (2014) Cobalt-catalyzed hydroarylative cyclization of 1,6-enynes with aromatic ketones and esters via C–H activation. Org Lett 16:4208–4211
  69.Fiebig L, Kuttner J, Hilt G, Schwarzer MC, Frenking G, Schmalz HG, Schäfer M (2013) Cobalt catalysis in the gas phase: experimental characterization of cobalt(I) complexes as intermediates in regioselective Diels–Alder reactions. J Org Chem 78:10485–10493CrossRef
  70.Sawano T, Ashouri A, Nishimura T, Hayashi T (2012) Cobalt-catalyzed asymmetric 1,6-addition of (triisopropylsilyl)-acetylene to α,β,γ,δ-unsaturated carbonyl compounds. J Am Chem Soc 134:18936–18939
  
• 作者单位：Qingxi Meng (1)
  Fen Wang (2)
  
  1. College of Chemistry and Material Science, Shandong Agricultural University, Taian, Shandong, 271018, People’s Republic of China
  2. Department of Chemistry, Taishan University, Taian, Shandong, 271021, People’s Republic of China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Biomedicine
  Molecular Medicine
  Health Informatics and Administration
  Life Sciences
  Computer Application in Life Sciences
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：0948-5023

文摘

Density functional theory (DFT) was used to study the cobalt(I)-catalyzed enantioselective intramolecular hydroacylation of ketones and alkenes. All intermediates and transition states were fully optimized at the M06/6-31G(d,p) level (LANL2DZ(f) for Co). The results demonstrated that the ketone and alkene present different reactivities in the enantioselective hydroacylation. In ketone hydroacylation catalyzed by the cobalt(I)–(R,R)-Ph-BPE complex, reaction channel “a” to (R)-phthalide was more favorable than channel “b” to (S)-phthalide. Hydrogen migration was both the rate-determining and chirality-limiting step, and this step was endothermic. In alkene hydroacylation catalyzed by the cobalt(I)–(R,R)-BDPP complex, reaction channel “c” leading to the formation of (S)-indanone was the most favorable, both thermodynamically and kinetically. Reductive elimination was the rate-determining step, but the chirality-limiting step was hydrogen migration, which occurred easily. The results also indicated that the alkene hydroacylation leading to (S)-indanone formation was more energetically favorable than the ketone hydroacylation that gave (R)-phthalide, both thermodynamically and kinetically.