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Pan, Xiangcheng (2014) CHEMISTRY AND APPLICATIONS OF N-HETEROCYCLIC CARBENE BORANES. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Chemistry and applications of N-heterocyclic carbene borane complex are demonstrated. Chapter 1 describes and introduces the background of NHC-boranes. Chapter 2 demonstrates the discovery and studies of thiol-catalyzed radical reduction reactions of alkyl and aryl halides with NHC-boranes. The radical reductive cyclization reactions with NHC-boranes were also investigated. These reactions occur by a polarity-reversal process, where thiol is the polarity-reversal catalysis. Chapter 3 describes the development and preparative experiments of first homolytic substitution reactions of NHC-boryl radicals at divalent atoms such as sulfur and selenium. The primary reaction products of heterocycle disulfides undergo a 1,3-boryl shift from S to N to give new class of stable NHC-boranes with B-N heterocycles bonds.
Chapter 4 describes the discovery that disulfides (RSSR), NHC-boryl mono- (NHC-BH2SR) and bis-sulfides (NHC-BH(SR)2) serve as both radical initiators and precatalysts in the radical reductions and reductive cyclizations with NHC-boranes. These reactions are also believed to occur by the polarity reversal catalysis mechanism. Chapter 5 describes the thiolation reactions with new synthesized NHC-boryl sulfides and –amido complexes. Chapter 6 introduces iodine-activated hydroboration and preliminary results of direct hydroboration.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberFloreancig, Paul Eflorean@pitt.eduFLOREAN
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberXie, Wenwex6@pitt.eduWEX6
Date: 24 September 2014
Date Type: Publication
Defense Date: 27 May 2014
Approval Date: 24 September 2014
Submission Date: 30 May 2014
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 202
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: NHC, carbene, borane, radical
Date Deposited: 24 Sep 2014 17:42
Last Modified: 15 Nov 2016 14:20


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