Nerkar, Swapnil
(2017)
Synthesis and Reactions of Alkyl- and Aryl-Substituted N-Heterocyclic Carbene Boranes.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
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.
Share
| Citation/Export: |
|
| Social Networking: |
|
Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| 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 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/33053 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Actions (login required)
 |
View Item |
![[feed]](/images/feed-icon-32x32.png){kind=icon}