Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki-Miyaura reactions

Tetrahedron Letters

Volumn 48, Issue 46, 2007, Pages 8242-8245

  Klingensmith, Liane M ^a   Bio, Matthew M ^a   Moniz, George A ^a  

^a AMGEN INC   (United States)

Author keywords

Lithiation; Protodeboronation; Regioselective; Suzuki

Indexed keywords

2 METHYL 3 THIOPHENEBORONIC ACID; 3 METHYLTHIOPHENE; 4 METHYL 2 THIOPHENEBORONIC ANHYDRIDE; ACID; BORIC ACID; BORONIC ACID DERIVATIVE; THIOPHENE DERIVATIVE; TRIISOPROPYLBORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; DEHYDRATION; HYDROLYSIS; ISOLATION PROCEDURE; MIYAURA REACTION; ORGANIC CHEMISTRY; PROTODEBORONATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 35348825460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.060     Document Type: Article

References (25)

1. Hall D.C. Boronic Acids: Preparation and Applications in Organic Synthesis and Methods (2005), Wiley, NY
2. For two reviews on the Suzuki-Miyaura reaction, see:. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
3. Suzuki A. J. Organomet. Chem. 576 (1999) 147-168
4. Periasamy M. Sci. Synth. 6 (2004) 301-320
5. Gerrard W. The Organic Chemistry of Boron (1961), Academic Press, London p 67-70
6. Li W., Nelson D.P., Jensen M.S., Hoerrner R.S., Cai D., Larsen R.D., and Reider P.J. J. Org. Chem. 67 (2002) 5394
7. For the synthesis of similar compounds in the literature:. Ye X.-S., and Wong H.N.C. Chem. Commun. (1996) 339-340
8. Dickinson R.P., and Iddon B. J. Chem. Soc. C (1970) 1926-1928
9. For several examples:. Kochanny M.J., Adler M., Ewing J., Griedel B.D., Ho E., Karanjawala R., Lee W., Lentz D., Liang A.M., Morrissey M.M., Phillips G.B., Post J., Sacchi K.L., Sakata S.T., Subramanyam B., Vergona R., Walters J., White K.A., Whitlow M., Ye B., Zhao Z., and Shaw K.J. Bioorg. Med. Chem. 15 (2007) 2127-2146
10. Poehler T., Schadt O., Niepel D., Rebernik P., Berger M.L., and Noe C.R. Eur. J. Med. Chem. 42 (2007) 175-197
11. Duplantier A.J., Bachert E.L., Cheng J.B., Cohan V.L., Jenkinson T.H., Kraus K.G., McKechney M.W., Pillar J.D., and Watson J.W. J. Med. Chem. 50 (2007) 344-349
12. Denton T.T., Zhang X., and Cashman J.R. J. Med. Chem. 48 (2005) 224
13. Conde S., Pérez D.I., Martínez A., Perez C., and Moreno F.J. J. Med. Chem. 46 (2003) 4631
14. Collins I., Moyes C., Davey W.B., Rowley M., Bromidge F.A., Quirk K., Atack J.R., McKernan R.M., Thompson S.-A., Wafford K., Dawson G.R., Pike A., Sohal B., Tsou N.N., Ball R.G., and Castro J.L. J. Med. Chem. 45 (2002) 1887
15. The regioselectivity is reported as 99:1 at -78 °C with a variety of electrophiles, not including boronates. Smith K., and Barratt M.L. J. Org. Chem. 72 (2007) 1031-1034
16. Gronowitz S., Cederlund B., and Hornfeldt A.-B. Chem. Scripta 5 (1974) 217-226
17. Kuivila H.G., and Nahabedian K.V. J. Am. Chem. Soc. 83 (1961) 2159
18. Kuivila H.G., and Nahabedian K.V. J. Am. Chem. Soc. 83 (1961) 2164
19. Nahabedian K.V., and Kuivila H.G. J. Am. Chem. Soc. 83 (1961) 2167
20. Florentin D., Fournie-Zaluski M.C., Callanquin M., and Roques B.P. J. Heterocycl. Chem. 13 (1976) 1265-1272
21. Brown R.D., Buchanan A.S., and Humffray A.A. Aust. J. Chem. 18 (1965) 1521-1525
22. Roques B.P., Florentin D., and Callanquin M. J. Heterocycl. Chem. 12 (1975) 195-196
23. 3: C, 48.44; H, 4.07; S, 25.87. Found: C, 48.55; H, 4.23; S, 25.78.
24. Huang X., Anderson K.W., Danilo Z., Jiang L., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 6653
25. For detailed experimental conditions and spectroscopic data, see Supplementary data.