Abstract
An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Albano G, Aronica LA (2017) Potentiality and synthesis of O- and N-heterocycles: Pd-catalyzed cyclocarbonylative sonogashira coupling as a valuable route to phthalans, isochromans, and isoindolines. Eur J Org Chem 48:7204–7221. https://doi.org/10.1002/ejoc.201701041
Albano G, Aronica LA (2018) Cyclization reactions for the synthesis of phthalans and isoindolines. Synthesis 50:1209–1227. https://doi.org/10.1055/s-0037-1609175
Alcaide B, Almendros P, Alonso JM (2011) Gold-catalyzed cyclizations of alkynol-based compounds: synthesis of natural products and derivatives. Molecules 16:7815–7843. https://doi.org/10.3390/molecules16097815
Aronica LA, Giannotti L, Tuci G, Zinna F (2015) Cyclocarbonylative sonogashira reactions of 1-ethynylbenzyl alcohols: synthesis of 1-carbonylmethylene-1,3-dihydroisobenzofurans. Eur J Org Chem 22:4944–4949. https://doi.org/10.1002/ejoc.201500539
Berg TC, Bakken V, Gundersen LL, Petersen D (2006) Cyclization and rearrangement products from coupling reactions between terminal o-alkynylphenols or o-ethynyl(hydroxymethyl)benzene and 6-halopurines. Tetrahedron 62:6121–6131. https://doi.org/10.1016/j.tet.2006.03.112
Brinkmann C, Barrett AGM, Hill MS, Procopiou PA, Reid S (2012) Alkaline earth catalysis of alkynyl alcohol hydroalkoxylation/cyclization. Organometallics 31:7287–7297. https://doi.org/10.1021/om3008663
Buxaderas E, Alonso DA, Nájera C (2014) Synthesis of dihydroisobenzofurans via palladium-catalyzed sequential alkynylation/annulation of 2-bromobenzyl and 2-chlorobenzyl alcohols under microwave irradiation. Adv Synth Catal 356:3415–3421. https://doi.org/10.1002/adsc.201400457
Cella JA, Bacon SW (1984) Preparation of dialkyl carbonates via the phase-transfer-catalyzed alkylation of alkali metal carbonate and bicarbonate salts. J Org Chem 49:1122–1125. https://doi.org/10.1021/jo00180a033
Chahdoura F, Mallet-Ladeira S, Gómez M (2015) Palladium nanoparticles in glycerol: a clear-cut catalyst for one-pot multi-step processes applied in the synthesis of heterocyclic compounds. Org Chem Front 2:312–318. https://doi.org/10.1039/C4QO00338A
Costello JP, Ferreira EM (2019) Regioselectivity influences in platinum-catalyzed intramolecular alkyne O–H and N–H additions. Org Lett 21:9934–9939. https://doi.org/10.1021/acs.orglett.9b03557
Doherty S, Knight JG, Perry DO, Ward NAB, Bitter DM, McFarlane W, Wills C, Probert MR (2016) Triaryl-Like MONO-, BIS-, and TRISKITPHOS phosphines: synthesis, solution NMR studies, and a comparison in gold-catalyzed carbon-heteroatom bond forming 5-exo-dig and 6-endo-dig cyclizations. Organometallics 35:1265–1278. https://doi.org/10.1021/acs.organomet.6b00146
Dorel R, Echavarren AM (2015) Gold(I)-catalyzed activation of alkynes for the construction of molecular complexity. Chem Rev 115:9028–9072. https://doi.org/10.1021/cr500691k
Dykstra CE, Arduengo AJ, Fukunaga FT (1978) A study of the vinyl anion system. Rearrangements and formation from hydride(1-) ion and acetylene. J Am Chem Soc 100:6007–6009. https://doi.org/10.1021/ja00487a005
Elliott RJ, Richards WG (1982) Quantitative frontier orbital theory: part II. A theoretical interpretation of the rules for ring closure. J Mol Struct (Theochem) 87:247–254. https://doi.org/10.1016/0166-1280(82)80004-3
Ersenstein O, Procter G, Dunitz JD (1978) Nucleophilic addition to a triple bond; preliminary ab initio study. Helv Chim Acta 61:2538–2541. https://doi.org/10.1002/hlca.19780610725
Fairley M, Davin L, Hernán-Gómez A, García-Álvarez J, O'Hara CT, Hevia E (2019) s-Block cooperative catalysis: alkali metal magnesiate-catalysed cyclisation of alkynols. Chem Sci 10:5821–5831. https://doi.org/10.1039/C9SC01598A
Flessner T, Doye S (1999) Cesium carbonate: a powerful inorganic base in organic synthesis. J Prakt Chem 341:186–190
Goodwin JA, Aponick A (2015) Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chem Commun 51:8730–8741. https://doi.org/10.1039/C5CC00120J
Hiroya K, Jouka R, Kameda M, Yasuhara A, Sakamoto T (2001) Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride. Tetrahedron 57:9697–9710. https://doi.org/10.1016/S0040-4020(01)00991-7
Jean A, Rouden J, Maddaluno J, De Paolis M, Blanchet J (2019) Catalytic and metal-free intramolecular hydroalkoxylation of alkynes. Tetrahedron Lett 60:534–537. https://doi.org/10.1016/j.tetlet.2019.01.0200040-4039
Karmakar R, Pahari P, Mal D (2014) Phthalides and phthalans: synthetic methodologies and their applications in the total synthesis. Chem Rev 114:6213–6284. https://doi.org/10.1021/cr400524q
Kobayashi K, Shikata K, Fukamachi S, Konishi H (2008) A facile synthesis of 1, 3-dihydroisobenzofurans using iodocylization of 2-vinylbenzyl alcohols. Heterocycles 75:599–609. https://doi.org/10.3987/COM-07-11244
Krishna Reddy AG, Satyanarayana G (2017) Palladium-catalyzed copper-free sonogashira coupling of 2-bromoarylcarbonyls: synthesis of isobenzofurans via one-pot reductive cyclization. Synthesis 49:5149–5158. https://doi.org/10.1055/s-0036-1588513
Li Y, Shi DKJ, Mao XF, Zhao ZL, Wu XY, Liu PN (2014) Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide. Tetrahedron 70:7022–7031. https://doi.org/10.1016/j.tet.2014.06.078
Mancuso R, Mehta S, Gabriele B, Salerno G, Jenks WS, Larock RC (2010) A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-alkynyl)benzylic alcohols. J Org Chem 75:897–901. https://doi.org/10.1021/jo902333y
Mandali PK, Pati AK, Mishra AK, Chand DK (2017) Fluorescent 1-arylidene-1,3-dihydroisobenzofuran: ligand-free palladium nanoparticles, catalyzed domino synthesis and photophysical studies. ChemistrySelect 2:5259–5265. https://doi.org/10.1002/slct.201700730
Mellor M, Santos A, Swrell EG, Sutherland JK (1978) Some epoxy-acetylene cyclisations. J Chem Soc Chem Commun 13:528–529. https://doi.org/10.1039/C39780000528
Perkins MJ, Wong PC, Barrett J, Shalival G (1981) Formation of dioxolanes from carbonyl compounds: favored 5-trigonal cyclizations. J Org Chem 46:2196–2199. https://doi.org/10.1021/jo00323a051
Pouy MJ, Delp SA, Uddin J, Ramdeen VM, Cochrane NA, Fortman GC, Gunnoe TB, Cundari TR, Sabat M, Myers WH (2012) Intramolecular hydroalkoxylation and hydroamination of alkynes catalyzed by Cu(I) complexes supported by N-heterocyclic carbene ligands. ACS Catal 2:2182–2193. https://doi.org/10.1021/cs300544w
Praveen C, Iyyappan C, Perumal PT (2010) Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols. Tetrahedron Lett 51:4667–4771. https://doi.org/10.1016/j.tetlet.2010.07.030
Praveen C, Iyyappan C, Perumal PT, Girija K (2012) AgOTf as an alternative catalyst for the regioselective cyclization of 2-(alkynyl) benzyl alcohols: synthesis and biological evaluation of phthalans. Indian J Chem 51B:498–507
Riediker M, Schwartz J (1982) Mercury(II)-induced cyclization of acetylenic alcohols: a new route to enol ethers and substituted enol ethers. J Am Chem Soc 104:5842–5844. https://doi.org/10.1021/ja00385a074
Sarbajna A, Pandey P, Rahaman SMW, Singh K, Tyagi A, Dixneuf PH (2017) A triflamide-tethered n-heterocyclic carbene-rhodium(i) catalyst for hydroalkoxylation reactions: ligand-promoted nucleophilic activation of alcohols. ChemCatChem 9:1397–1401. https://doi.org/10.1002/cctc.201601667
Seo SY, Yu XH, Marks T (2009) Intramolecular hydroalkoxylation/cyclization of alkynyl alcohols mediated by lanthanide catalysts. Scope and reaction mechanism. J Am Chem Soc 131:263–276. https://doi.org/10.1021/ja8072462
Shang XS, Li DY, Li NT, Liu PN (2015) A concise synthesis of tunable fluorescent 1,3-dihydroisobenzofuran derivatives as new fluorophores. Dyes Pigm 114:8–17. https://doi.org/10.1016/j.dyepig.2014.10.013
Shishkina IN, Sokolovskava EY, Demynovich VM (2016) Stereoselective synthesis of 1,3-disubstituted phthalans by cyclization of (1S)-1-{2-[hydroxy(diaryl)methyl]phenyl}ethanols. Russ Chem Bull 65:2229–2232. https://doi.org/10.1007/s11172-016-1573-y
Strozier RW, Caramella P, Houk KN (1979) Influence of molecular distortions upon reactivity and stereochemistry in nucleophilic additions to acetylenes. J Am Chem Soc 101:1340–1343. https://doi.org/10.1021/ja00499a078
Tomás-Mendivil E, Starck J, Ortuno JC, Michelet V (2015) Synthesis of functionalized 1H-isochromene derivatives via a Au-catalyzed domino cycloisomerization/reduction approach. Org Lett 17:6126–6129. https://doi.org/10.1021/acs.orglett.5b03146
Vandavasi JK, Hu WP, Senadi GC, Bominathan SSK, Chen HY, Wang JJ (2014) A K2CO3-mediated regioselective synthesis of indole/pyrrole-fused 1,4-oxazines: an unexpected indole-fused azlactone synthesis. Eur J Org Chem 28:6219–6226. https://doi.org/10.1002/ejoc.201402818
Weingarten MD, Padwa A (1995) Intramolecular addition to an unactivated carbon-carbon triple bond via an apparent 6-endo digonal pathway. Tetrahedron Lett 36:4717–4720. https://doi.org/10.1016/0040-4039(95)00891-F
Wobser SD, Marks TJ (2013) Organothorium-catalyzed hydroalkoxylation/cyclization of alkynyl alcohols. scope, mechanism, and ancillary ligand effects. Organometallics 32:2517–2628. https://doi.org/10.1021/om300881b
Yang X, Pan S, Cheng F, Lin YW, Yuan Q, Zhang FL, Huang YY (2017) Enantioselective synthesis of 1,3-disubstituted 1,3-dihydroisobenzofurans via a cascade allylboration/oxo-michael reaction of o-formyl chalcones catalyzed by a chiral phosphoric acid. J Org Chem 82:10388–10397. https://doi.org/10.1021/acs.joc.7b01856
Yu SY, Wu JX, Lan HB, Xu HW, Shi XF, Zhu XW, Yin ZG (2018) Transition metal/Brønsted acid cooperative catalysis enabled facile synthesis of 8-hydroxyquinolines through one-pot reactions of ortho-aminophenol, aldehydes and alkynes. RSC Adv 8:33968–33971. https://doi.org/10.1039/C8RA07212D
Yu SY, Wu JX, Lan HB, Gao LH, Qian HY, Fan KQ, Yin ZG (2020) Palladium and brønsted acid Co-catalyzed Biginelli-like multicomponent reactions via in situ-generated cyclic enol ether: access to spirofuran-hydropyrimidinones. Org Lett 22:102–105. https://doi.org/10.1021/acs.orglett.9b04015
Acknowledgements
The authors are grateful for the support from the National Natural Science Foundation of China (21602207), the Foundation of Henan Educational Committee (17A150022), and the Doctoral Research Fund of Zhengzhou University of Light Industry (2014BSJJ009).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
On behalf of all authors, the corresponding author states that there is no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.11
Rights and permissions
About this article
Cite this article
Yu, SY., Gao, LH., Wu, JX. et al. Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions. Chem. Pap. 74, 3303–3310 (2020). https://doi.org/10.1007/s11696-020-01159-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-020-01159-5