Copper(II) and Bismuth(III)
Hydroxide Catalyzed Addition Reactions of Hydrazonoester
with Allenylboronate in Aqueous Media

Shu Kobayashi; Taku Kitanosono; Masaharu Ueno

doi:10.1055/s-0030-1258485

CLUSTER

Copper(II) and Bismuth(III) Hydroxide Catalyzed Addition Reactions of Hydrazonoester with Allenylboronate in Aqueous Media

Shu Kobayashi*, Taku Kitanosono, Masaharu Ueno
Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences,, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 110-0033, Japan
Fax: +81(3)56840634; e-Mail: shu_kobayashi@chem.s.u-tokyo.ac.jp;

Abstract

All articles of this category

Abstract

Metal-hydroxide-catalyzed addition reactions of hydrazonoester with allenylboronate in aqueous media are described. The propargyl adduct was obtained selectively by using copper(II) hydroxide, whereas the allenyl adduct was produced preferentially using bismuth(III) hydroxide in water-DMF (1:3). The reactions proceeded smoothly in pure water without the use of any organic solvents by addition of a small amount (1.7 mol%) of sucrose.

Key words

allenylation - propargylation - hydrazones - green chemistry - chemoselectivity

Full Text

References

References and Notes

1a Aqueous-Phase Organometallic Catalysis 2nd ed.: Cornils B. Herrmann WA. Wiley-VCH; Weinheim: 2004.

1b Organic Reactions in Water Lindström UM. Blackwell; Oxford: 2007.

1c Kobayashi S. Pure Appl. Chem. 2007, 79: 235

1d Ogawa C. Kobayashi S. In Catalytic Asymmetric Synthesis 3rd ed.: Ojima I. Wiley-VCH; Weinheim: 2010. p.1-35

Recent works:

2a Kokubo M. Ogawa C. Kobayashi S. Angew. Chem. Int. Ed. 2008, 47: 6909

2b Nagano T. Kobayashi S. Chem. Lett. 2008, 37: 1042

2c Kokubo M. Kobayashi S. Chem. Asian J. 2009, 4: 526

2d Kokubo M. Naito T. Kobayashi S. Chem. Lett. 2009, 38: 904

2e Kokubo M. Naito T. Kobayashi S. Tetrahedron 2010, 66: 1111

2f Kobayashi S. Kokubo M. Kawasumi K. Kobayashi S. Chem. Asian J. 2010, 5: 490

Metal hydroxide or hydrous metal-oxide-catalyzed reactions, see:

3a Krause A. Urbanowicz M. Naturwissenschaften 1963, 50: 473

3b Tsuji J. Nagashima T. Qui NT. Takayanagi H. Tetrahedron 1980, 36: 1311

3c Matsushita H. Ishiguro S. Ichinose H. Izumi A. Mizusaki S. Chem. Lett. 1985, 731

3d Shibagaki M. Takahashi K. Matsushita H. Bull. Chem. Soc. Jpn. 1988, 61: 3283

3e Takahashi K. Shibagaki M. Kuno H. Kawakami H. Matsushita H. Bull. Chem. Soc. Jpn. 1989, 62: 1333

3f Onishi Y. Ogawa D. Yasuda M. Baba A. J. Am. Chem. Soc. 2002, 124: 13690

3g Liamas R. Jiménez-Sanchidrián C. Ruiz JR. React. Kinet. Catal. Lett. 2007, 90: 309

Recent studies of supported metal hydroxide on metal oxide catalyzed reactions, see:

4a Wang N. Li J. Zhu L. Dong Y. Tang H. J. Photochem. Photobiol. A: Chem. 2008, 198: 282

4b Oishi T. Katayama T. Yamaguchi K. Mizuno N. Chem. Eur. J. 2009, 15: 7539

4c He J. Kim JW. Yamaguchi K. Mizuno N. Angew. Chem. Int. Ed. 2009, 48: 9888

5 Fujita M. Nagano T. Schneider U. Hamada T. Ogawa C. Kobayashi S. J. Am. Chem. Soc. 2008, 130: 2914

6 Kobayashi S. Endo T. Schneider U. Ueno M. Chem. Commun. 2010, 46: 1260

For examples, see:

7a Song Y. Okamoto S. Sato F. Tetrahedron Lett. 2002, 43: 8635

7b Kumareswaran R. Gallucci J. RajanBabu TV. J. Org. Chem. 2004, 69: 9151

7c Kaden S. Brockmann M. Reißig H.-U. Helv. Chim. Acta 2005, 88: 1826

7d Ferreia F. Botuha C. Chemla F. Pérez-Luna A. J. Org. Chem. 2009, 74: 2238

Lewis acid catalyzed allenylation or propargylation:

8a Jin J. Smith DT. Weinreb SM. J. Org. Chem. 1995, 60: 5366

8b Weinreb SM. Smith DT. Jin J. Synthesis 1998, 509

8c Kagoshima H. Uzawa T. Akiyama T. Chem. Lett. 2002, 31: 298

8d Fuchibe K. Hatemata R. Akiyama T. Tetrahedron Lett. 2005, 46: 8563

8e Fuchibe K. Heremata R. Akiyama T. Tetrahedron 2006, 62: 11304

8f Hirashita T. Kawai D. Araki S. Tetrahedron Lett. 2007, 48: 5421

Selected examples of synthetic method for propargylation adducts, see:

9a Brown HC. Khire UR. Narla G. Racherla US. J. Org. Chem. 1995, 60: 544

9b Poisson J.-F. Normant JF. J. Org. Chem. 2000, 65: 6553

9c Poisson J.-F. Normant JF. J. Am. Chem. Soc. 2001, 123: 4639

9d Gonzalez AZ. Soderquist JA. Org. Lett. 2007, 9: 1081

9e Séguin C. Ferreira F. Botuha C. Chemla F. Pérez-Luna A. J. Org. Chem. 2009, 74: 6986

9f Fandrick DR. Johnson CS. Fandrick KR. Reeves JT. Tan Z. Lee H. Song JJ. Yee NK. Senanayake CH. Org. Lett. 2010, 12: 748

Selected examples of synthetic method for allenylation adducts, see:

10a Amombo MO. Hausherr A. Reißig H.-U. Synlett 1999, 1871

10b Breuil-Desvergnes V. Goré J. Tetrahedron 2001, 57: 1951

10c Kang H.-Y. Yu Y.-K. Bull. Korean Chem. Soc. 2004, 25: 1627

10d Piao X. Jung J.-K. Kang H.-Y. Bull. Korean Chem. Soc. 2007, 28: 139

Selected other examples, see:

11a Nikan SS. Wang KK. J. Org. Chem. 1985, 50: 2193

11b Miyabe H. Yamaoka Y. Naito T. Takemoto Y. J. Org. Chem. 2004, 69: 1415

11c Yanagisawa A. Suzuki T. Koide T. Okitsu S. Arai T. Chem. Asian J. 2008, 3: 1793

11d Guan X.-Y. Wei Y. Shi M. J. Org. Chem. 2009, 74: 6343

11e Cowen BJ. Saunders LB. Miller SJ. J. Am. Chem. Soc. 2009, 131: 6105

12a Schneider U. Sugiura M. Kobayashi S. Adv. Synth. Catal. 2006, 348: 323

12b Schneider U. Sugiura M. Kobayashi S. Tetrahedron 2006, 62: 496

13 Recently, we report that Ag₂O-catalyzed anti-selective α-addition of α-substituted allyltributyltin with aldehydes in aqueous media: Ueno M. Tanoue A. Kobayashi S. Chem. Lett. 2010, 39: 652

14a Banerjee M. Roy S. Chem. Commun. 2003, 534

14b Banerjee M. Roy S. Org. Lett. 2004, 6: 2137

15

It was confirmed that isomerization of 5 did not occur.

16a Kobayashi S. Manabe K. Pure Appl. Chem. 2000, 72: 1373

16b Mori Y. Manabe K. Kobayashi S. Angew. Chem. Int. Ed. 2001, 40: 2815

16c Kobayashi S. Manabe K. Acc. Chem. Res. 2002, 35: 209

16d Mori Y. Kobayashi J. Manabe K. Kobayashi S. Tetrahedron 2002, 58: 8263