Easy access to pharmaceutically relevant heterocycles by catalytic reactions involving α-imino gold carbene intermediates

Springer Science and Business Media LLC - Tập 14 Số 3 - Trang 317-349 - 2020
Ximei Zhao1, Matthias Rudolph1, Abdullah M. Asiri2, A. Stephen K. Hashmi2,1
1Organisch-Chemisches Institut, Heidelberg University, Heidelberg, Germany
2Chemistry Department, Faculty of Science, Jeddah, Saudi Arabia

Tóm tắt

Từ khóa


Tài liệu tham khảo

Hashmi A S K, Frost T M, Bats J W. Highly selective gold-catalyzed arene synthesis. Journal of the American Chemical Society, 2000, 122(46): 11553–11554

Hashmi A S K, Schwarz L, Choi J H, Frost T M. A new gold-catalyzed C–C bond formation. Angewandte Chemie International Edition in English, 2000, 39(13): 2285–2288

Hann M M, Leach A R, Harper G. Molecular complexity and its impact on the probability of finding leads for drug discovery. Journal of Chemical Information and Computer Sciences, 2001, 41(3): 856–864

Fürstner A. Gold and platinum catalysis—a convenient tool for generating molecular complexity. Chemical Society Reviews, 2009, 38(11): 3208–3221

Pflästerer D, Hashmi A S K. Gold catalysis in total synthesis-recent achievements. Chemical Society Reviews, 2016, 45(5): 1331–1367

Asiri A M, Hashmi A S K. Gold-catalysed reactions of diynes. Chemical Society Reviews, 2016, 45(16): 4471–4503

Hashmi A S K, Frost T M, Bats J W. Gold catalysis: On the phenol synthesis. Organic Letters, 2001, 3(23): 3769–3771

Reetz M T, Sommer K. Gold-catalyzed hydroarylation of alkynes. European Journal of Organic Chemistry, 2003, 2003(18): 3485–3496

Dyker G, Muth E, Hashmi A S K, Ding L. Gold(III) chloride-catalyzed addition reactions of electron-rich arenes to methyl vinyl ketone. Advanced Synthesis & Catalysis, 2003, 345(11): 1247–1252

Nevado C, Echavarren A M. Intramolecular hydroarylation of alkynes catalyzed by platinum or gold: Mechanism and endo selectivity. Chemistry (Weinheim an der Bergstrasse, Germany), 2005, 11(10): 3155–3164

Buzas A, Gagosz F. Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates. Organic Letters, 2006, 8(3): 515–518

Gagosz F. Unusual gold(I)-catalyzed isomerization of 3-hydroxylated 1,5-enynes: Highly substrate-dependent reaction manifolds. Organic Letters, 2005, 7(19): 4129–4132

Revol G, McCallum T, Morin M, Gagosz F, Barriault L. Photoredox transformations with dimeric gold complexes. Angewandte Chemie International Edition in English, 2013, 52(50): 13342–13345

Xie J, Zhang T, Chen F, Mehrkens N, Rominger F, Rudolph M, Hashmi A S K. Gold-catalyzed highly selective photoredox C (sp2)-H difluoroalkylation and perfluoroalkylation of hydrazones. Angewandte Chemie International Edition in English, 2016, 55(8): 2934–2938

Huang L, Rudolph M, Rominger F, Hashmi A S K. Photosensitizer-free visible light-mediated gold-catalyzed 1,2-difunctionalization of alkynes. Angewandte Chemie International Edition in English, 2016, 55(15): 4808–4813

Huang L, Rominger F, Rudolph M, Hashmi A S K. A general access to organogold(III) complexes by oxidative addition of diazonium salts. Chemical Communications, 2016, 52(38): 6435–6438

Xie J, Sekine K, Witzel S, Kramer P, Rudolph M, Rominger F, Hashmi A S K. Light-induced gold-catalyzed hiyama arylation: A coupling access to biarylboronates. Angewandte Chemie International Edition in English, 2018, 57(51): 16648–16653

Witzel S, Sekine K, Rudolph M, Hashmi A S K. New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer. Chemical Communications, 2018, 54(98): 13802–13804

Witzel S, Xie J, Rudolph M, Hashmi A S K. Photosensitizer-free, gold-catalyzed C–C cross-coupling of boronic acids and diazonium salts enabled by visible light. Advanced Synthesis & Catalysis, 2017, 359(9): 1522–1528

Xie J, Shi S, Zhang T, Mehrkens N, Rudolph M, Hashmi A S K. A highly efficient gold-catalyzed photoredox α-C(sp3)-H alkynylation of tertiary aliphatic amines with sunlight. Angewandte Chemie International Edition in English, 2015, 54(20): 6046–6050

Braun I, Asiri A M, Hashmi A S K. Gold catalysis 2.0. ACS Catalysis, 2013, 3(8): 1902–1907

Greisch J F, Weis P, Brendle K, Kappes M M, Haler J R N, Far J, De Pauw E, Albers C, Bay S, Wurm T, et al. Detection of intermediates in dual gold catalysis using high-resolution ion mobility mass spectrometry. Organometallics, 2018, 37(9): 1493–1500

Hashmi A S K, Braun I, Rudolph M, Rominger F. The role of gold acetylides as a selectivity trigger and the importance of gemdiaurated species in the gold-catalyzed hydroarylating-aromatization of arene-diynes. Organometallics, 2012, 31(2): 644–661

Hashmi A S K. Dual gold catalysis. Accounts of Chemical Research, 2014, 47(3): 864–876

Plajer A J, Ahrens L, Wieteck M, Lustosa D M, Babaahmadi R, Yates B, Ariafard A, Rudolph M, Rominger F, Hashmi A S K. Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by dual gold catalysis competition experiments. Chemistry (Weinheim an der Bergstrasse, Germany), 2018, 24(42): 10766–10772

Liu L, Xu B, Mashuta M S, Hammond G B. Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations. Journal of the American Chemical Society, 2008, 130(52): 17642–17643

Weber D, Tarselli M A, Gagne M R. Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes. Angewandte Chemie International Edition in English, 2009, 48(31): 5733–5736

Hashmi A S K, Schuster A M, Rominger F. Gold catalysis: Isolation of vinylgold complexes derived from alkynes. Angewandte Chemie International Edition in English, 2009, 48(44): 8247–8249

Nunes Dos Santos Comprido L, Klein J, Knizia G, Kastner J, Hashmi A S K. On the accessible reaction channels of vinyl gold(I) species: π- and σ-pathways. Chemistry (Weinheim an der Bergstrasse, Germany), 2017, 23(45): 10901–10905

Hashmi A S K. Isolable vinylgold intermediates—first access to phantoms of homogeneous gold catalysis. Gold Bulletin, 2009, 42(4): 275–279

Fructos M R, Belderrain T R, de Frémont P, Scott N M, Nolan S P, Díaz-Requejo M M, Pérez P J. A Gold catalyst for carbene—transfer reactions from ethyl diazoacetate. Angewandte Chemie International Edition in English, 2005, 44(33): 5284–5288

Fürstner A, Morency L. On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions. Angewandte Chemie International Edition in English, 2008, 47(27): 5030–5033

Johansson M J, Gorin D J, Staben S T, Toste F D. Gold(I)-catalyzed stereoselective olefin cyclopropanation. Journal of the American Chemical Society, 2005, 127(51): 18002–18003

Xia Y, Dudnik A S, Gevorgyan V, Li Y. Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: Ligand-controlled regioselectivity. Journal of the American Chemical Society, 2008, 130(22): 6940–6941

Klein J E, Knizia G, Nunes dos Santos Comprido L, Kästner J, Hashmi A S K C. (sp3)–H bond activation by vinylidene gold(I) complexes: A concerted asynchronous or stepwise process? Chemistry (Weinheim an der Bergstrasse, Germany), 2017, 23(63): 16097–16103

Nunes dos Santos Comprido L, Klein J E, Knizia G, Kastner J, Hashmi A S K. The stabilizing effects in gold carbene complexes. Angewandte Chemie International Edition in English, 2015, 54(35): 10336–10340

Fürstner A, Hannen P. Carene terpenoids by gold-catalyzed cycloisomerization reactions. Chemical Communications, 2004, 22: 2546–2547

Fürstner A, Hannen P. Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates: Total syntheses of (-)-α-cubebene, (-)-cubebol, sesquicarene and related terpenes. Chemistry (Weinheim an der Bergstrasse, Germany), 2006, 12(11): 3006–3019

Wang Y, Zheng Z, Zhang L. Intramolecular insertions into unactivated C(sp3)-H bonds by oxidatively generated β-diketone-α-gold carbenes: Synthesis of cyclopentanones. Journal of the American Chemical Society, 2015, 137(16): 5316–5319

Li J, Ji K, Zheng R, Nelson J, Zhang L. Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: Efficient oxidative union of allylic sulfides and terminal alkynes via C–C bond formation. Chemical Communications, 2014, 50(31): 4130–4133

Shu C, Li L, Xiao X, Yu Y, Ping Y, Zhou J, Ye L. Flexible and practical synthesis of 3-oxyindoles through gold-catalyzed inter-molecular oxidation of o-ethynylanilines. Chemical Communications, 2014, 50(63): 8689–8692

Gorin D J, Davis N R, Toste F D. Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction. Journal of the American Chemical Society, 2005, 127(32): 11260–11261

Witham C A, Mauleón P, Shapiro N D, Sherry B D, Toste F D. Gold (I)-catalyzed oxidative rearrangements. Journal of the American Chemical Society, 2007, 129(18): 5838–5839

Lu B, Luo Y, Liu L, Ye L, Wang Y, Zhang L. Umpolung reactivity of indole through gold catalysis. Angewandte Chemie International Edition in English, 2011, 50(36): 8358–8362

Wetzel A, Gagosz F. Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient eccess to the valuable pseudoindoxyl and indolyl frameworks. Angewandte Chemie International Edition in English, 2011, 123(32): 7492–7496

Li N, Wang T, Gong L, Zhang L. Gold-catalyzed multiple cascade reaction of 2-alkynylphenylazides with propargyl alcohols. Chemistry (Weinheim an der Bergstrasse, Germany), 2015, 21(9): 3585–3588

Tokimizu Y, Oishi S, Fujii N, Ohno H. Gold-catalyzed cascade cyclization of (azido)ynamides: An efficient strategy for the construction of indoloquinolines. Organic Letters, 2014, 16(11): 3138–3141

Shen C, Pan Y, Yu Y, Wang Z, He W, Li T, Ye L. Facile and efficient synthesis of [1,4]oxazino[3,2-b]indoles and 1H-pyrazino[2,3-b] indoles through gold-catalyzed cascade cyclization of (azido) ynamides. Journal of Organometallic Chemistry, 2015, 795: 63–67

Pan Y, Chen G, Shen C, He W, Ye L. Synthesis of fused isoquinolines via gold-catalyzed tandem alkyne amination/intramolecular O–H insertion. Organic Chemistry Frontiers: An International Journal of Organic Chemistry/Royal Society of Chemistry, 2016, 3(4): 491–495

Xiao Y, Zhang L. Synthesis of bicyclic imidazoles via [2 + 3] cycloaddition between nitriles and regioselectively generated α-Imino gold carbene intermediates. Organic Letters, 2012, 14(17): 4662–4665

Yan Z Y, Xiao Y, Zhang L. Gold-catalyzed one-step construction of 2,3-dihydro-1H-Pyrrolizines with an electron-withdrawing group in the 5-position: A formal synthesis of 7-methoxymitosene. Angewandte Chemie International Edition in English, 2012, 51(34):8624–8627

Zhu S, Wu L, Huang X. Gold-catalyzed cyclization of 3-(2′-azidoaryl)-1-arylpropargyl carbonates or 3-aryl-1-(2′-azidoaryl)propargyl carbonates to produce quinolines. Journal of Organic Chemistry, 2013, 78(18): 9120–9126

Loy N S Y, Choi S, Kim S, Park C. The synthesis of pyrroles and oxazoles based on gold α-imino carbene complexes. Chemical Communications, 2016, 52(46): 7336–7339

Prechter A, Henrion G, Faudot dit Bel P, Gagosz F. Gold-catalyzed synthesis of functionalized pyridines by using 2H-azirines as synthetic equivalents of alkenyl nitrenes. Angewandte Chemie International Edition in English, 2014, 53(19): 4959–4963

Shu C, Wang Y H, Zhou B, Li X L, Ping Y F, Lu X, Ye L. Generation of α-Imino gold carbenes through gold-catalyzed intermolecular reaction of azides with ynamides. Journal of the American Chemical Society, 2015, 137(30): 9567–9570

Davies P W, Cremonesi A, Dumitrescu L. Intermolecular and selective synthesis of 2,4,5-trisubstituted oxazoles by a gold-catalyzed formal [3 + 2] cycloaddition. Angewandte Chemie International Edition in English, 2011, 50(38): 8931–8935

Reddy R J, Ball-Jones M P, Davies P W. Alkynyl thioethers in gold-catalyzed annulations to form oxazoles. Angewandte Chemie International Edition in English, 2017, 56(43): 13310–13313

Li C, Zhang L. Gold-catalyzed nitrene transfer to activated alkynes: Formation of α, β-unsaturated amidines. Organic Letters, 2011, 13(7): 1738–1741

González J, Santamaría J, Suárez-Sobrino Á L, Ballesteros A. One-pot and regioselective gold-catalyzed synthesis of 2-imidazolyl-1-pyrazolylbenzenes from 1-propargyl-1H-benzotriazoles, alkynes and nitriles through α-imino gold(I) carbene complexes. Advanced Synthesis & Catalysis, 2016, 358(9): 1398–1403

Zhu L, Yu Y, Mao Z, Huang X. Gold-catalyzed intermolecular nitrene transfer from 2H-azirines to ynamides: A direct approach to polysubstituted pyrroles. Organic Letters, 2015, 17(1): 30–33

Zhou A, He Q, Shu C, Yu Y, Liu S, Zhao T, Zhang W, Lu X, Ye L. Atom-economic generation of gold carbenes: Gold-catalyzed formal [3 + 2] cycloaddition between ynamides and isoxazoles. Chemical Science (Cambridge), 2015, 6(2): 1265–1271

Sahani R, Liu R S. Development of gold-catalyzed [4 + 1] and [2 + 2 + 1]/[4 + 2] annulations between propiolate derivatives and isoxazoles. Angewandte Chemie International Edition in English, 2017, 56(4): 1026–1030

Kardile R D, Kale B S, Sharma P, Liu R. Gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles to construct a pyrrole core. Organic Letters, 2018, 20(13): 3806–3809

Chen M, Sun N, Chen H, Liu Y. Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: Highly efficient synthesis of functionalized oxazoles. Chemical Communications, 2016, 52(37): 6324–6327

Zeng Z, Jin H, Xie J, Tian B, Rudolph M, Rominger F, Hashmi A S K. α-Imino gold carbenes from 1,2,4-oxadiazoles: Atom-economical access to fully substituted 4-aminoimidazoles. Organic Letters, 2017, 19(5): 1020–1023

Xu W, Wang G, Sun N, Liu Y. Gold-catalyzed formal [3 + 2] cycloaddition of ynamides with 4,5-dihydro-1,2,4-oxadiazoles: Synthesis of functionalized 4-aminoimidazoles. Organic Letters, 2017, 19(12): 3307–3310

Jin H, Huang L, Xie J, Rudolph M, Rominger F, Hashmi A S K. Gold-catalyzed C–H annulation of anthranils with alkynes: A facile, flexible, and atom-economical synthesis of unprotected 7-acylindoles. Angewandte Chemie International Edition in English, 2016, 55(2): 794–797

Zeng Z, Jin H, Sekine K, Rudolph M, Rominger F, Hashmi A S K. Gold-catalyzed regiospecific C–H annulation of o-ethynylbiaryls with anthranils: π-Extension by ring-expansion en route to N-doped PAHs. Angewandte Chemie International Edition in English, 2018, 57(23): 6935–6939

Tian X, Song L, Farshadfar K, Rudolph M, Rominger F, Oeser T, Hashmi A S K. Acyl migrations versus epoxidations in gold catalyis: Facile, switchable and atom-economic synthesis of acylindoles and quinoline derivatives. Angewandte Chemie International Edition in English, 2019, in press, DOI: https://doi.org/10.1002/anie.201912334

Jin H, Tian B, Song X, Xie J, Rudolph M, Rominger F, Hashmi A S K. Gold-catalyzed synthesis of quinolines from propargyl silyl ethers and anthranils through the umpolung of a gold carbene carbon. Angewandte Chemie International Edition in English, 2016, 55(41): 12688–12692

Tsai M H, Wang C, Kulandai Raj A S, Liu R. Gold-catalyzed annulations of N-aryl ynamides with benzisoxazoles to construct 6H-indolo[2,3-b]quinoline cores. Chemical Communications, 2018, 54(77): 10866–10869

Patil M D, Liu R. Direct access to benzofuro[2,3-b]quinoline and 6H-chromeno[3,4-b] quinoline cores through gold-catalyzed annulation of anthranils with arenoxyethynes and aryl propargyl ethers. Organic & Biomolecular Chemistry, 2019, 17(18): 4452–4455

Zeng Z, Jin H, Rudolph M, Rominger F, Hashmi A S K. Gold(III)-catalyzed site-selective and divergent synthesis of 2-aminopyrroles and quinoline-based polyazaheterocycles. Angewandte Chemie International Edition in English, 2018, 57(50): 16549–16553

Hsieh H C, Tan K C, Kulandai Raj A S, Liu R S. Gold-catalyzed [4 + 1]-annulation reactions between anthranils and 4-methoxy-1, 2-dienyl-5-ynes involving a 1,2-allene shift. Chemical Communications, 2019, 55(13): 1979–1982

Jadhav P D, Lu X, Liu R. Gold-catalyzed [5 + 2]- and [5 + 1]-annulations between ynamides and 1,2-benzisoxazoles with ligand-controlled chemoselectivity. ACS Catalysis, 2018, 8(10): 9697–9701

Xu W, Zhao J, Li X, Liu Y. Selective [5 + 1] and [5 + 2] cycloaddition of ynamides or propargyl esters with benzo[d] isoxazoles via gold catalysis. Journal of Organic Chemistry, 2018, 83(24): 15470–15485

Yu Y, Chen G, Zhu L, Liao Y, Wu Y, Huang X. Gold-catalyzed βregioselective formal [3 + 2] cycloaddition of ynamides with pyrido[1,2-b]indazoles: Reaction development and mechanistic insights. Journal of Organic Chemistry, 2016, 81(18): 8142–8154

Tian X, Song L, Rudolph M, Rominger F, Oeser T, Hashmi A S K. Sulfilimines as versatile nitrene transfer reagents: Facile access to diverse aza-heterocycles. Angewandte Chemie International Edition in English, 2019, 58(11): 3589–3593

Tian X, Song L, Rudolph M, Wang Q, Song X, Rominger F, Hashmi A S K. N-pyridinyl sulfilimines as a source for α-imino gold carbenes: Access to 2-amino-substituted N-fused imidazoles. Organic Letters, 2019, 21(6): 1598–1601

Tian X, Song L, Han C, Zhang C, Wu Y, Rudolph M, Rominger F, Hashmi A S K. Gold(III)-catalyzed formal [3 + 2] annulations of N-acyl sulfilimines with ynamides for the synthesis of 4-aminooxazoles. Organic Letters, 2019, 21(8): 2937–2940