Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Synthesis and Reactions of Alkyl- and Aryl-Substituted N-Heterocyclic Carbene Boranes

Nerkar, Swapnil (2017) Synthesis and Reactions of Alkyl- and Aryl-Substituted N-Heterocyclic Carbene Boranes. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

Updated Version

Download (3MB) | Preview


Synthesis and applications of alkyl- and aryl-substituted NHC-boranes has been demonstrated. Chapter 1 shows the synthesis of methyl- and phenyl-substituted NHC-boranes by using organolithium reagents. Other alkyl- and aryl-substituted NHC-boranes have been prepared by hydroboration of alkenes and arynes respectively. The prepared substituted NHC-boranes were converted to Suzuki coupling precursors such as boronic acids, trifluoroborate salts, pinacol boronate esters and MIDA boronates. Fluorinated NHC-boranes were made by electrophilic fluorination of NHC-boranes with Selectfluor. The diMe-Imd-BF2H has been synthesized via the use of a nucleophilic fluorination source (TBAF). The corresponding boryl radical has been generated and its properties have been compared to the boryl radical of the parent diMe-Imd-BH3.
Chapter 2 describes the use of B-halo substituted NHC-boranes in the Suzuki coupling reactions. The NHC-(dibromo)arylboranes are converted to the boronic acids in-situ while the NHC-(difluoro)arylboranes are analogous to potassium trifluoroborate salts and used directly in the Suzuki coupling reaction. The potential for the use of NHC-(difluoro)arylboranes as a boron masking partner has been demonstrated. NHC-(difluoro)pinylborane has been used in the Minisci reaction showcasing the utility of NHC-boranes as a new boron partner in the C-C bond formation reactions.


Social Networking:
Share |


Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Nerkar, Swapnilssn9@pitt.edussn9
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran,
Committee MemberFloreancig,
Committee MemberHorne,
Committee MemberVanDemark,
Date: 28 September 2017
Date Type: Publication
Defense Date: 4 August 2017
Approval Date: 28 September 2017
Submission Date: 10 August 2017
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 151
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-Boranes, Suzuki Coupling
Date Deposited: 28 Sep 2017 22:55
Last Modified: 28 Sep 2017 22:55


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item