A Mild and Efficient Synthesis
of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ6-sulfanyl
Group

Maxim V. Ponomarenko; Yurii A. Serguchev; Gerd-Volker Röschenthaler

doi:10.1055/s-0030-1258254

PAPER

A Mild and Efficient Synthesis of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ⁶-sulfanyl Group

Maxim V. Ponomarenko*^a,b, Yurii A. Serguchev^a, Gerd-Volker Röschenthaler*^b
^a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya Str., 02094 Kiev, Ukraine
Fax: +38(44)5732643; e-Mail: maxponom@yahoo.co.uk;
^b School of Engineering and Science, Jacobs University Bremen gGmbH, Campus Ring 1, 28759 Bremen, Germany
Fax: +49(241)2003229; e-Mail: g.roeschenthaler@jacobs-university.de;

Abstract

All articles of this category

Abstract

An efficient four-step route towards the synthesis of conjugated 1,3-dienes substituted with a terminal SF₅-group was proposed. Key steps of the synthetic sequence are the bromination of 1-(pentafluoro-λ⁶-sulfanyl)alk-1-enes followed by dehydrobromination of the corresponding products.

Key words

butadienes - alkenes - pentafluorosulfanyl group - elimination

Full Text

References

<A NAME="RT13810SS-1A">1a</A> Müller M. Faeh C. Diederich F. Science 2007, 317: 1881

<A NAME="RT13810SS-1B">1b</A> Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008, 37: 320

<A NAME="RT13810SS-1C">1c</A> Kirk KL. Org. Process Res. Dev. 2008, 12: 305

<A NAME="RT13810SS-2A">2a</A> Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Application Kirsch P. Wiley-VCH; Weinheim: 2004.

<A NAME="RT13810SS-2B">2b</A> Ye C. Gard GL. Winter RW. Syvret RG. Twamley B. Shreeve JM. Org. Lett. 2007, 9: 3841

<A NAME="RT13810SS-2C">2c</A> Winter RW. Dodean RA. Gard GL. In Fluorine-Containing Synthons, ACS Symposium Series 911 Soloshonok VA. American Chemical Society; Washington DC: 2005. p.87-118

<A NAME="RT13810SS-2D">2d</A> Kirsch P. Röschenthaler G.-V. In Current Fluoroorganic Chemistry - New Synthetic Directions, Technologies, Materials, and Biological Applications, ACS Symposium Series 949 Soloshonok VA. Mikami K. Yamazaki T. Welch JT. Honek JF. American Chemical Society; Washington DC: 2007. p.221

<A NAME="RT13810SS-2E">2e</A> Welch JT. Lim DS. Bioorg. Med. Chem. 2007, 15: 6659

<A NAME="RT13810SS-2F">2f</A> Lal GS. Syvret RG. Chim. Oggi 2008, 26: 26

<A NAME="RT13810SS-2G">2g</A> Lentz D. Seppelt K. In Chemistry of Hypervalent Compounds Akiba K. Wiley-VCH; Weinheim: 1999. p.295-325

<A NAME="RT13810SS-3A">3a</A> Salmon R. inventors; WO 9,306,089.

<A NAME="RT13810SS-3B">3b</A> Howard MH, and Stevenson TM. inventors; WO 9,516,676.

<A NAME="RT13810SS-4">4</A> Crowley PJ. Mitchell G. Salmon R. Worthington PA. Chimia 2004, 58: 138

<A NAME="RT13810SS-5">5</A> Kirsch P. Binder JT. Lork E. Röschenthaler G.-V.
J. Fluorine Chem. 2006, 127: 610

<A NAME="RT13810SS-6A">6a</A> St. Clair TL, St. Clair AK, and Thrasher JS. inventors; US 5,220,070.

<A NAME="RT13810SS-6B">6b</A> Winter RW. Nixon PG. Gard GL. Castner DG. Holcomb NR. Hu Y.-H. Grainger DW. Chem. Mater. 1999, 11: 3044

<A NAME="RT13810SS-7">7</A> Abe T. Tao G.-H. Joo Y.-H. Winter RW. Gard GL. Shreeve JM. Chem. Eur. J. 2009, 15: 9897

<A NAME="RT13810SS-8A">8a</A> Nishino S, Shima H, Omata Y, and Oda H. inventors; WO 2009,028,514.

<A NAME="RT13810SS-8B">8b</A> Kirsch P, Tarumi K, and Krause J. inventors; DE 19,748,108.

<A NAME="RT13810SS-9A">9a</A> Brel VK. J. Fluorine Chem. 2007, 128: 862

<A NAME="RT13810SS-9B">9b</A> Brel VK. Synthesis 2005, 1245

<A NAME="RT13810SS-9C">9c</A> Brel VK. Synthesis 2006, 339

<A NAME="RT13810SS-10">10</A> Case JR. Ray NH. Roberts HL. J. Chem. Soc. 1961, 2066

<A NAME="RT13810SS-11A">11a</A> Aït-Mohand S. Dolbier WR. Org. Lett. 2002, 4: 3013

<A NAME="RT13810SS-11B">11b</A> Dolbier WR. Mitani A. Xu W. Ghiviriga I. Org. Lett. 2006, 8: 5573

<A NAME="RT13810SS-11C">11c</A> Dolbier WR. Aït-Mohand S. Schertz TD. Sergeeva TA. Cradlebaugh JA. Mitani A. Gard GL. Winter RW. Thrasher JS. J. Fluorine Chem. 2006, 127: 1302

<A NAME="RT13810SS-12">12</A> Winter RW. Gard GL. J. Fluorine Chem. 2008, 129: 1041

<A NAME="RT13810SS-13">13</A> Lim DS. Ngo SC. Lal SG. Minnich KE. Welch JT. Tetrahedron Lett. 2008, 49: 5662

<A NAME="RT13810SS-14">14</A> Ponomarenko MV. Serguchev YA. Röschenthaler G.-V. J. Fluorine Chem. 2010, 131: 270

<A NAME="RT13810SS-15A">15a</A> Hoover FW. Coffman DD. J. Org. Chem. 1964, 29: 3567

<A NAME="RT13810SS-15B">15b</A> Sergeeva TA. Dolbier WR. Org. Lett. 2004, 6: 2417

<A NAME="RT13810SS-15C">15c</A> Winter RW. Gard GL. J. Fluorine Chem. 2004, 125: 549

<A NAME="RT13810SS-16">16</A> Dolbier WR. Zheng Z. J. Org. Chem. 2009, 74: 5626

<A NAME="RT13810SS-17">17</A> Klauck A. Seppelt K. Angew. Chem., Int. Ed. Engl. 1994, 33: 93

<A NAME="RT13810SS-18">18</A> Winter RW. Dodean R. Holmes L. Gard GL. J. Fluorine Chem. 2004, 125: 37

<A NAME="RT13810SS-19A">19a</A> Cignarella G. Pasqualucci CR. Gallo GG. Testa E. Tetrahedron 1964, 20: 1057

<A NAME="RT13810SS-19B">19b</A> Trushkov IV. Brel VK. Tetrahedron Lett. 2005, 46: 4777

A Mild and Efficient Synthesis of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ6-sulfanyl Group

A Mild and Efficient Synthesis of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ⁶-sulfanyl Group