Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes

M. Carmen Carreño; Marcos González-López; Alfonso Latorre; Antonio Urbano

doi:10.1055/s-2005-869857

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Synlett 2005(10): 1601-1605
DOI: 10.1055/s-2005-869857

LETTER

Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes

M. Carmen Carreño*, Marcos González-López, Alfonso Latorre, Antonio Urbano*
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain
Fax: 34(91)4973966; e-Mail: carmen.carrenno@uam.es; e-Mail: antonio.urbano@uam.es;

Further Information

Publication History

Received 20 April 2005
Publication Date:
07 June 2005 (online)

Abstract
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Abstract

Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes occurred preferentially at the A-ring when no substituents were present at the ortho-positions of the aryl group (up to 100% selectivity), to afford 1-aryl-7-methoxy-1,2,3,4-tetrahydronaphthalenes. Ortho-substitution of the 1-aryl moiety favored B-ring reduction (up to 85:15 selectivity) giving rise, after acidic hydrolysis of the vinyl ether intermediate, to the corresponding 8-aryl-2-tetralones.

Key words

biaryls - chemoselectivity - steric hindrance - reductions - sodium

References

1 Harvey RG. Lindow DF. Rabideau PW. J. Am. Chem. Soc. 1972, 94: 5412

Crossref Google Scholar
2a Rabideau PW. Marcinow Z. J. Org. Chem. 1990, 55: 3812

Google Scholar
2b Eisenbraun EJ. Melton RG. Flanagan PW. Hamming MC. Keen GW. Prepr.-Am. Chem. Soc., Div. Pet. Chem. 1971, 16: B43

Google Scholar
Recent examples:
3a Tririya G. Zanger M. Synth. Commun. 2004, 34: 3047

Crossref Google Scholar
3b Silveira CC. Machado A. Braga AL. Lenardao EJ. Tetrahedron Lett. 2004, 45: 4077

Crossref Google Scholar
3c Barolo SM. Lukach AE. Rossi RA. J. Org. Chem. 2003, 68: 2807

Crossref Google Scholar
3d Renaud JL. Dupau P. Hay A.-E. Guingouain M. Dixneuf PH. Bruneau C. Adv. Synth. Catal. 2003, 345: 230

Crossref Google Scholar
Recent examples:
4a Jha A. Beal J. Tetrahedron Lett. 2004, 45: 8999

Crossref Google Scholar
4b Li D. Zhao B. Sim S.-P. Li T.-K. Liu A. Liu LF. LaVoie EJ. Bioorg. Med. Chem. 2003, 11: 521

Crossref Google Scholar
4c Wang X.-Z. Yao Z.-J. Liu H. Zhang M. Yang D. George C. Burke TR. Tetrahedron 2003, 59: 6087

Crossref Google Scholar
Recent examples:
5a Youngman MA. Willard NM. Dax SL. McNally JJ. Synth. Commun. 2003, 33: 2215

Crossref Google Scholar
5b Gemma S. Butini S. Fattorusso C. Fiorini I. Nacci V. Bellebaum K. McKissic D. Saxenac A. Campiani G. Tetrahedron 2003, 59: 87

Crossref Google Scholar
Reviews:
6a Silveira CC. Braga AL. Kaufman TS. Lenardao EJ. Tetrahedron 2004, 60: 8295

Google Scholar
6b Schner VF. Przhiyaglovskaya NM. Russ. Chem. Rev. 1966, 35: 523

Google Scholar
7a Chen F. Feng X. Qin B. Zhang G. Jiang Y. Synlett 2003, 558

Google Scholar
7b Alcock LJ. Mann I. Peach P. Wills M. Tetrahedron: Asymmetry 2002, 13: 2485

Google Scholar
7c Parker MH. Chen R. Conway KA. Lee DHS. Luo C. Boyd RE. Nortey SO. Ross TM. Scorr MK. Reitz AB. Bioorg. Med. Chem. 2002, 10: 3565

Google Scholar
8a Hirayama Y. Ikunaka M. Matsumoto J. Org. Process Res. Dev. 2005, 30

Crossref Google Scholar
8b Banerjee AK. Vera WJ. J. Chem. Res., Synop. 2004, 135

Crossref Google Scholar
8c Cheung AW.-H. Danho W. Swistok J. Qi L. Kurylko G. Rowan K. Yeon M. Franco L. Chu X.-J. Chen L. Yagaloff K. Bioorg. Med. Chem. Lett. 2003, 13: 133

Crossref Google Scholar
8d Jha A. Dimmock JR. Can. J. Chem. 2003, 81: 293

Crossref Google Scholar
8e Taber DF. Neubert TD. Rheingold AL. J. Am. Chem. Soc. 2002, 124: 12416

Crossref Google Scholar
9a Li D. Zhao B. Sim S.-P. Li T.-K. Liu A. Liu LF. LaVoie EJ. Bioorg. Med. Chem. 2003, 11: 3795

Crossref Google Scholar
9b Makhey D. Li D. Zhao B. Sim S.-P. Li TK. Liu A. Liu LF. LaVoie EJ. Bioorg. Med. Chem. 2003, 11: 1809

Crossref Google Scholar
9c Maguire AR. O’Leary P. Harrington F. Lawrence SE. Blake AJ. J. Org. Chem. 2001, 66: 7166

Crossref Google Scholar
10a Oishi S. Kang SU. Liu H. Zhang M. Yang D. Deschamps JR. Burke TR. Tetrahedron 2004, 60: 2971

Crossref Google Scholar
10b Gray AD. Smith TP. J. Org. Chem. 2001, 66: 7113

Crossref Google Scholar
11a Carreño MC. González-López M. Urbano A. Chem. Commun. 2005, 611

Crossref Google Scholar
11b Carreño MC. García-Cerrada S. Urbano A. Chem.-Eur. J. 2003, 9: 4118-4131

Crossref Google Scholar
11c Carreño MC. García-Cerrada S. Urbano A. Chem. Commun. 2002, 1412

Crossref Google Scholar
11d Carreño MC. García-Cerrada S. Urbano A. J. Am. Chem. Soc. 2001, 123: 7929

Crossref Google Scholar
12a Ram VJ. Agarwal N. Saxena AS. Farhanullah . Sharon A. Maulik PR. J. Chem. Soc., Perkin Trans. 1 2002, 1426

Crossref Google Scholar
12b Ram VJ. Agarwal N. Farhanullah . Tetrahedron Lett. 2002, 43: 3281

Crossref Google Scholar
13 Soffer MD. Bellis MP. Gellerson HE. Stewart RA. Org. Synth. 1952, 32: 97

Google Scholar
14 Cornforth JW. Cornforth RH. Robinson R. J. Chem. Soc. 1942, 689

Google Scholar
15a Carreño MC. García-Cerrada S. Sanz-Cuesta MJ. Urbano A. Chem. Commun. 2001, 1452-1453

Google Scholar
15b
Carreño, M. C.; Enríquez, A.; García-Cerrada, S.; Sanz-Cuesta, M. J.; Urbano, A. unpublished results.
16 Birch AJ. J. Chem. Soc. 1944, 430

Crossref Google Scholar
17a Harvey RG. Synthesis 1970, 161

Google Scholar
17b Rabideau PW. Tetrahedron 1989, 45: 1579

Google Scholar
17c Rabideau PW. Marcinow Z. Org. React. 1992, 42: 1

Google Scholar
For examples on the additions of aryl Grignard reagents to α-tetralones see:
18a Alcock NJ. Mann I. Peach P. Wills M. Tetrahedron: Asymmetry 2002, 13: 2485

Article in Thieme Connect Google Scholar
18b Schneider MR. Schiller CD. Arch. Pharm. 1990, 323: 17

Article in Thieme Connect Google Scholar
18c Laus G. Tourwe D. Van Binst G. Heterocycles 1984, 22: 311

Article in Thieme Connect Google Scholar
18d Adam G. Andrieux J. Plat M. Tetrahedron 1982, 38: 2403

Article in Thieme Connect Google Scholar
18e Bindal RD. Durani S. Kapil RS. Anand N. Synthesis 1982, 405

Article in Thieme Connect Google Scholar
19a Suzuki A. Modern Arene Chemistry Wiley-VCH; New York: 2002. p.53

Article in Thieme Connect Google Scholar
19b Miyaura N. Suzuki A. Chem. Rev. 1995. 95: p.2457

Article in Thieme Connect Google Scholar
For examples of cross-coupling reactions between enol triflates and boronic acids and derivatives see:
19c Miyashita K. Sakai T. Imanishi T. Org. Lett. 2003, 5: 2683

Article in Thieme Connect Google Scholar
19d Basil LF. Nakano H. Frutos R. Kopach M. Meyers AI. Synthesis 2002, 2064

Article in Thieme Connect Google Scholar
19e Pal K. Synthesis 1995, 1485

Article in Thieme Connect Google Scholar
20 Watanabe T. Miyaura N. Suzuki A. Synlett 1992, 207

Article in Thieme Connect Google Scholar
21 Scheiper B. Bonnekessel M. Krause H. Fürstner A. J. Org. Chem. 2004, 69: 3943

Crossref PubMed Google Scholar
22 Boronic acids 7d-h were commercially available (7d-f and 7h) or previously described: 7g: Bringmann G. Goetz R. Keller PA. Walter R. Boyd MR. Lang F. Garcia A. Walsh JJ. Tellitu I. Bhaskar KV. Kelly TR. J. Org. Chem. 1998, 63: 1090

Crossref Google Scholar
23 The ¹H NMR spectrum (CDCl₃) of compound 8g showed several broad non-well resolved signals probably due to the presence of atropisomers caused by a hindered rotation about the aryl(sp²)-C₁(sp³) single bond: Eliel EL. Wilen SH. Doyle MP. In Basic Organic Stereochemistry Wiley; New York: 2001. p.629 ; when 8g was heated in C₂D₂Cl₄ at 390 K the broad signals coalesced

Google Scholar
24 Carey FA. Sundberg RJ. In Advanced Organic Chemistry. Part B: Reactions and Synthesis 4th ed.: Kluwer; Norwell: 2000.

Google Scholar