IDiyas

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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 9328102 B1

PDFFull Text
Date of Patent:
May. 03, 2016

Filed:

Apr. 14, 2015

Slow release of organoboronic acids in cross-coupling reactions

Applicant:

The Board of Trustees of the University of Illinois, Urbana, IL (US);

Inventors:

Martin D. Burke, Champaign, IL (US);

David M. Knapp, Boonville, IN (US);

Eric P. Gillis, Wallingford, CT (US);

Assignee:

The Board of Trustees of the University of Illinois, Urbana, IL (US);

Attorneys:

Alan W. Steele

Foley Hoag LLP

Primary Examiner:

Charanjit Aulakh

Int. Cl.
CPC ...
C07F 5/02 (2006.01); C07F 5/04 (2006.01); C07D 413/04 (2006.01); C07C 1/32 (2006.01); C07C 41/30 (2006.01); C07D 207/325 (2006.01); C07D 213/73 (2006.01); C07D 241/42 (2006.01); C07D 263/56 (2006.01); C07D 307/42 (2006.01); C07D 401/04 (2006.01); C07D 405/12 (2006.01); C07D 409/04 (2006.01); C07B 61/00 (2006.01); C07D 207/333 (2006.01); C07D 209/12 (2006.01); C07D 307/36 (2006.01); C07D 307/80 (2006.01); C07D 333/16 (2006.01); C07D 405/04 (2006.01);
U.S. Cl.
CPC ...
C07D 413/04 (2013.01); C07B 61/00 (2013.01); C07C 1/321 (2013.01); C07C 41/30 (2013.01); C07D 207/325 (2013.01); C07D 207/333 (2013.01); C07D 209/12 (2013.01); C07D 213/73 (2013.01); C07D 241/42 (2013.01); C07D 263/56 (2013.01); C07D 307/36 (2013.01); C07D 307/42 (2013.01); C07D 307/80 (2013.01); C07D 333/16 (2013.01); C07D 401/04 (2013.01); C07D 405/04 (2013.01); C07D 405/12 (2013.01); C07D 409/04 (2013.01); C07C 2101/02 (2013.01); C07C 2531/24 (2013.01); Y02P 20/55 (2015.11);
Abstract

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R—B-T  (I);where Rrepresents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sphybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKof at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

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