Direct nucleophilic C-1 addition of stable isochromenylium tetrafluoroborates under catalyst-free conditions: A new access to 1H-isochromenes

Science China Chemistry

Volumn 53, Issue 4, 2010, Pages 869-876

  Hu, Zhi Long ^a   Qian, Wen Jian ^a   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Isochromene; Isochromenylium; Nucleophilic addition

Indexed keywords

CATALYST-FREE; ISOCHROMENES; MILD TEMPERATURES; NUCLEOPHILIC ADDITIONS; TETRAFLUOROBORATES;

CATALYSTS;

ADDITION REACTIONS;

EID: 77953301817     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-0129-5     Document Type: Article

References (30)

1. Xu YC, Lebeau E, Gillard JW, Attardo G. Regio-and stereoselective DDQ-induced oxidative coupling of isochromans and isothiochroman with alcohols. Tetrahedron Lett, 1993, 34: 3841-3844 (Pubitemid 23179447)
2. Kueny-Stotz M, Isorez G, Chassaing S, Brouillard R. Straightforward synthesis of highly hydroxylated phloroglucinol-type 3-deoxyanthocyanidins. Synlett, 2007, 1067-1070 (Pubitemid 46715900)
3. Mutter R, Campbell IB, Martin de la Nava EM, Merritt AT, Wills M. Palladium-catalyzed tandem reactions to form 1-vinyl-1H-isochromene derivatives. J Org Chem, 2001, 66: 3284-3290 (Pubitemid 32878934)
4. Qian WJ, Wei WG, Zhang YX, Yao ZJ. Total synthesis, assignment of absolute stereochemistry, and structural revision of chlorofusin. J Am Chem Soc, 2007, 129: 6400-6401 (Pubitemid 46799338)
5. Wei WG, Zhang YX, Yao ZJ. Efficient construction of novel α-keto spiro ketal and the total synthesis of (±)-terreinol. Tetrahedron, 2005, 61: 11882-11886
6. Zhu JL, Germain AR, Porco Jr JA. Synthesis of azaphilones and related molecules by employing cycloisomerization of o-alkynylbenzaldehydes. Angew Chem Int Ed, 2004, 43: 1239-1243
7. Wei WG, Yao ZJ. Synthesis studies toward chloroazaphilone and vinylogous γ-pyridones: Two common natural product core structures. J Org Chem, 2005, 70: 4585-4590
8. Yao YS, Yao ZJ. Biomimetic total syntheses of cassiarins A and B. J Org Chem, 2008, 73: 5221-5225
9. 2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: A new synthetic method for functionalized polycyclic hydrocarbons. J Org Chem, 2005, 70: 3682-3685 (Pubitemid 40577580)
10. Hildebrandt D, Dyker G. A gold-catalyzed domino process to the steroid framework. J Org Chem, 2006, 71: 6728-6733 (Pubitemid 44645646)
11. Asao N, Takahashi K, Yamamoto Y. AuCl3-catalyzed benzannulation: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes. J Am Chem Soc, 2002, 124: 12650-12651 (Pubitemid 35215975)
12. Li ZG, Brouwer C, He C. Gold-catalyzed organic transformations. Chem Rev, 2008, 108: 3239-3265
13. Shen HC. Recent advances in syntheses of carbocycles and heterocycles via homogeneous gold catalysis. part 2: Cyclizations and cycloadditions. Tetrahedron, 2008, 64: 7847-7870
14. Beeler AB, Su S, Singleton CA, Porco Jr JA. Discovery of chemical reactions through multidimensional screening. J Am Chem Soc, 2007, 129: 1413-1419 (Pubitemid 46208614)
15. 2-catalyzed [4+2] cycloaddition of oalkynyl( oxo)benzenes with alkenes. Angew Chem Int Ed, 2003, 42: 3504-3506
16. 3. Tetrahedron Lett, 2002, 43: 5673-5676 (Pubitemid 34786538)
17. Asao N, Kasahara T, Yamamoto Y. Pd(II) acts simultaneously as a lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes. J Am Chem Soc, 2002, 124: 764-765 (Pubitemid 34112781)
18. Kusama H, Funami H, Shido M, Iwasawa N. Generation and reaction of tungsten-containing carbonyl ylides: [3+2]-Cycloaddition reaction with electron-rich alkenes. J Am Chem Soc, 2005, 127: 2709-2716 (Pubitemid 40327833)
19. Kusama H, Ishida K, Funami H, Iwasawa N. Platinum (II)-catalyzed reaction of gamma, delta-ynones with alkenes for the construction of 8-oxabicyclo[3.2.1]octane skeletons: generation of platinum-containing carbonyl ylides from acyclic precursors. Angew Chem Int Ed, 2008, 47: 4903-4905
20. Wei LM, Lin CF, Wu MJ. Palladium-catalyzed coupling of aryl iodides with 2-alkynylbenzonitriles. Tetrahedron Lett, 2000, 41: 1215-1218 (Pubitemid 30117338)
21. Hildebrandt D, Hüggenberg W, Kanthak M, Dyker G. A platinumcatalyzed annulation reaction leading to medium-sized rings. Chem Commun, 2006, 2260-2261 (Pubitemid 43800892)
22. Bruneau C. Electrophilic activation and cycloisomerization of enynes: a new route to functional cyclopropanes. Angew Chem Int Ed, 2005, 44: 2328-2334 (Pubitemid 40600211)
23. Barluenga J, Vázquez-Villa H, Ballesteros A, González JM. Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: A versatile trigger for assembling oxygen heterocycles. J Am Chem Soc, 2003, 125: 9028-9029 (Pubitemid 36903819)
24. Goldfinger MB, Crawford KB, Swager TM. Fused polycyclic aromatics via electrophile-induced cyclization reactions: Application to the synthesis of graphite ribbons. J Am Chem Soc, 2003, 1994, 116: 7895-7896
25. Barluenga J, Vázquez-Villa H, Merino I, Ballesteros A, González JM. The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: A versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds. Chem Eur J, 2006, 12: 5790-5805 (Pubitemid 44179188)
26. Yue D, Cá ND, Larock RC. Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones. Org Lett, 2004, 6: 1581-1584 (Pubitemid 38698456)
27. Waldo JP, Larock RC. The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib. J Org Chem, 2007, 72: 9643-9647 (Pubitemid 350231812)
28. Hu ZL, Qian WJ, Wang S, Wang SZ, Yao ZJ. Transformation of reactive isochromenylium intermediates to stable salts and their cascade reactions with olefins. Org Lett, 2009, 11: 4676-4679
29. Hu ZL, Qian WJ, Wang S, Wang SZ, Yao ZJ. Construction of multiring frameworks by metal-free cascade reactions of stable isochromenylium tetrafluoroborate. J Org Chem, 2009, 74: 8787-8793
30. Lotagawa O, Inoue T, Taguchi T. Iodocarbocyclization reaction. Rev Heteroatom Chem, 1996, 15: 243-262. (Pubitemid 126175453)