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Development of Cu- and Ni-Catalyzed C–C and C–N Bond Forming Reactions

Citation

Bachman, Shoshana (2017) Development of Cu- and Ni-Catalyzed C–C and C–N Bond Forming Reactions. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z99S1P2G. http://resolver.caltech.edu/CaltechTHESIS:06042017-233801526

Abstract

Chapters 1 and 2 describe the development of photoinduced, Cu-catalyzed coupling reactions of unactivated secondary alkyl halides with amide and cyanide nucleophiles. These reactions may be conducted at room temperature under operationally simple conditions. Mechanistic studies are consistent with the intermediacy of alkyl radicals in these processes.

Chapter 3 describes progress toward the development of the first enantioselective Ni-catalyzed cross coupling of racemic alkyl halides and heteroatom nucleophiles. Borylation of secondary benzylic chlorides with B2(pin)2 may be achieved in good yield and promising levels of enantioselectivity.

Chapter 4 describes enantioselective Ni-catalyzed couplings of α-substituted lactam enolates with benzonitrile derivatives resulting in formal intermolecular C- acylation via in situ hydrolysis of an imine intermediate.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Catalysis, Reaction Development, Methodology, Ni catalysis, Cu catalysis, Asymmetric Catalysis
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Reisman, Sarah E. (chair)
  • Fu, Gregory C.
  • Peters, Jonas C.
  • Stoltz, Brian M.
Defense Date:25 May 2017
Record Number:CaltechTHESIS:06042017-233801526
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:06042017-233801526
DOI:10.7907/Z99S1P2G
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja4126609DOIArticle related to Chapter 1
http://dx.doi.org/10.1021/jacs.5b08452DOIArticle related to Chapter 2
http://dx.doi.org/10.1021/jacs.6b02120DOIArticle related to Chapter 4
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10271
Collection:CaltechTHESIS
Deposited By: Shoshana Bachman
Deposited On:06 Jun 2017 23:56
Last Modified:15 Jun 2017 16:57

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