{"id":{"repo_id":"mit","oai_identifier":"oai:dspace.mit.edu:1721.1/62101"},"canonical_url":"https://search.dev.ndltd.org/etd/mit/oai:dspace.mit.edu:1721.1/62101","repository":{"repo_id":"mit","name":"MIT","base_url":"https://dspace.mit.edu/oai/request"},"display":{"title":"Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Lu, Zhe"],"institution":"Massachusetts Institute of Technology","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":"Massachusetts Institute of Technology. Department of Chemistry","school":null,"contributors":[],"advisors":["Gregory C. Fu."],"committee_chairs":[],"committee_members":[],"year":2010,"date_issued":"2010","date_published":"2010","updated_at":"2026-07-22T22:20:46Z","subjects":["Chemistry."],"languages":["eng"],"rights":["M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission."],"rights_urls":["http://dspace.mit.edu/handle/1721.1/7582"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/1721.1/62101","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Gregory C. Fu."]},{"key":"dc:contributor.department","label":"Department","values":["Massachusetts Institute of Technology. Department of Chemistry"]},{"key":"dc:contributor.other","label":"Dc Contributor Other","values":["Massachusetts Institute of Technology. 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They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission."]},{"key":"dc:rights.uri","label":"Rights URI","values":["http://dspace.mit.edu/handle/1721.1/7582"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/1721.1/62101"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2010.","Vita. Cataloged from PDF version of thesis.","Includes bibliographical references."]},{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph.D."]},{"key":"dc:title","label":"Title","values":["Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions"]}]}],"canonical_facts":{"dc:contributor.advisor":["Gregory C. Fu."],"dc:contributor.department":["Massachusetts Institute of Technology. Department of Chemistry"],"dc:contributor.other":["Massachusetts Institute of Technology. Dept. of Chemistry."],"dc:creator":["Lu, Zhe"],"dc:date.accessioned":["2011-04-04T17:41:07Z"],"dc:date.available":["2011-04-04T17:41:07Z"],"dc:date.issued":["2010"],"dc:description":["Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2010.","Vita. 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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."],"dc:description.degree":["Ph.D."],"dc:identifier.uri":["http://hdl.handle.net/1721.1/62101"],"dc:language.iso":["eng"],"dc:publisher":["Massachusetts Institute of Technology"],"dc:rights":["M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission."],"dc:rights.uri":["http://dspace.mit.edu/handle/1721.1/7582"],"dc:subject":["Chemistry."],"dc:title":["Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions"],"dc:type":["Thesis"]},"updated_at":"2026-07-22T22:20:46Z"}