CAS Science Spotlight Most Requested Documents 4Q02-Chemistry and Related Science


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Most Requested Documents 4Q02-Chemistry and Related Science

Following is one of the documents most requested by researchers using CAS electronic products.

CAS indexed 39 chemical substances from this document.
CAS subject entries for this document include: Acids, reactions; Group IIIA element compounds; Crystal structure; and 4 additional concepts.

TITLE:	Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions
AUTHOR(S):	Kirchhoff, Jan H.; Netherton, Matthew R.; Hills, Ivory D.; Fu, Gregory C.
CORPORATE SOURCE:	Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA
SOURCE:	Journal of the American Chemical Society (2002), 124(46), 13662-13663 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chem., and boronic acids are, by far, the most commonly employed coupling partner. To date, however, no versatile method has been developed for cross-coupling boronic acids with unactivated alkyl (as opposed to aryl or vinyl) electrophiles. This report describes a catalyst system that achieves this objective at room temp. On the mechanistic side, this study demonstrates that Pd(P(t-Bu)2Me)2 undergoes oxidative addn. under surprisingly mild conditions (0 .degree.C). The resulting adduct is sufficiently stable toward .beta.-hydride elimination that it can be structurally characterized, and it is a chem. competent intermediate in the cross-coupling process.

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Updated 5/11/2007 9:07:56 AM