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Title:
PROCESS FOR MAKING ORGANOBORON COMPOUNDS, PRODUCTS OBTAINABLE THEREBY, AND THEIR USE
Document Type and Number:
WIPO Patent Application WO/2012/085170
Kind Code:
A3
Abstract:
A process for making organoboron compounds is disclosed in which at least one organic compound having at least one Cl, Br, or I atom or at least one nucleophilic leaving group substituent is reacted with at least one boron-containing reagent represented by the chemical formula (IA) or (IB): B(YR1)3 (IA) [Cat]n+[B(YR1)4 -]n (IB) in the presence of at least one oxidizable metal or oxidizable metal complex, wherein each Y independently represents an oxygen atom, a sulfur atom, or −NR'-, each R1 and each R' independently represents an organic moiety comprising up to 15 carbon atoms and, optionally, one or more hetero atoms, Cat is a cation or mixture of cations, and n is a positive number in the range from 1 to 3. The organoboron products obtained by this process are useful for conducting coupling reactions and reactions with aldehydes. Due to their selectivity, such reactions may be conducted in protic solvents, such as water and alcohols, and sensitive functional groups in the reactants are maintained in the final product. The organoboron products are stable, so that they maintain their activity during storage.

Inventors:
HAAG BENJAMIN (DE)
KNOCHEL PAUL (DE)
Application Number:
PCT/EP2011/073716
Publication Date:
October 26, 2012
Filing Date:
December 22, 2011
Export Citation:
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Assignee:
HAAG BENJAMIN (DE)
International Classes:
C07F5/05; C07C67/00; C07D307/60; C07D343/00; C07F5/04
Other References:
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"Suspensions: Fundamentals and Applications in the Petroleum Industry", vol. 42, 1 January 1964, AMERICAN CHEMICAL SOCIETY, Washington, DC, ISSN: 0065-2393, article DIETMAR SEYFERTH ET AL: "Synthesis of B-Organofunctional Borazine Derivatives", pages: 259 - 265, XP055027652
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ADONIN NICOLAY YU ET AL: "Polyfluoroorganoboron-oxygen compounds. 4. Lithium pentafluorophenyltrimethoxyborate, Li[C6F5B(OMe)3], reactions with selected electrophiles and nucleophiles", ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 631, no. 13-14, 1 October 2005 (2005-10-01), pages 2638 - 2646, XP009161320, ISSN: 0044-2313, [retrieved on 20051019]
ADONIN NICOLAI YU ET AL: "Polyfluoroorganoboron-oxygen compounds. 7+. Studies of conversion of [(C6HnF5-n)B(OMe)3]- into [(C6HnF5-n)2B(OMe)2]- (n = 0, 1)", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, INSTITUTE OF ORGANIC CHEMISTRY & BIOCHEMISTRY, PRAGUE; CZ, vol. 73, no. 12, 1 January 2008 (2008-01-01), pages 1681 - 1692, XP009161323, ISSN: 0010-0765, DOI: 10.1135/CCCC20081681
ANULEWICZ-OSTROWSKA ROMANA ET AL: "Synthesis and characterization of bromomagnesium[(bispentafluorophenyl)diethoxyborate]", MAIN GROUP METAL CHEMISTRY, TEL AVIV, IL, vol. 25, no. 8, 1 January 2002 (2002-01-01), pages 501 - 504, XP009161324, ISSN: 0792-1241
KLIS TOMASZ ET AL: "Formation of arylboron compounds from arylmagnesium reagents and trialkoxyboranes", MAIN GROUP METAL CHEMISTRY, TEL AVIV, IL, vol. 25, no. 8, 1 January 2002 (2002-01-01), pages 479 - 484, XP009161325, ISSN: 0792-1241, DOI: 10.1515/MGMC.2002.25.8.479
Attorney, Agent or Firm:
LELKES, Robert (Munich, DE)
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