Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions
Name
707926392-MIT.pdf
Description
Full printable version
Size
7.09 MB
Format
Adobe PDF
Checksum (MD5)
20be2baf406850c8f2765f3611a49939
Author(s)
Lu, Zhe
Advisor(s)
Gregory C. Fu.
Date Issued
2010
Publisher
Massachusetts Institute of Technology
Abstract
Part I describes the expansion in scope of a nickel-catalyzed coupling reaction of unactivated alkyl bromides and alkyl boranes to include unactivated alkyl chlorides. The new method is adapted for use outside of a glove box and is also found to be applicable not only to the coupling of primary chlorides, but also to the coupling of bromides and iodides, both primary and secondary. ... This coupling reaction of chlorides is further adapted to the of p-chloro aryl alkyl amines. This work constitutes an extension directing groups for the asymmetric Suzuki-Miyaura reactions halides. ... Part II details work towards an asymmetric Diels-Alder reaction between cyclopentadiene and methacrolein catalyzed by a planar-chiral boron Lewis acid. This system exhibits a level of turnover that is unprecedented in reactions mediated by planar chiral boron heterocycles. Computational studies shed light on the nature of the 7tsymmetry interaction between borabenzenes and complexed carbonyl groups. The selectivity of the borabenzene-catalyzed Diels-Alder reaction is also examined.
Description
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2010.
Vita. Cataloged from PDF version of thesis.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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