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Studies on the total synthesis of gambierol via endo-selective epoxide-opening cascades
(Massachusetts Institute of Technology, 2016)
Progress towards the total synthesis of gambierol inspired by the biosynthetic hypothesis for ladder polyethers is described. Syntheses of the ABCD and FGH fragments have been completed in 29 and 3 1 steps, respectively, ...
The Pd-catalyzed fluorination of (hetero)aryl bromides and triflates
(Massachusetts Institute of Technology, 2015)
Chapter 1: This chapter details mechanistic work regarding the reductive elimination of electron-rich aryl fluorides from L-Pd(Ar)F species. An unexpected dearomatization/arylation process of Pd(II) complexes bearing bulky ...
New Pd and Cu-based catalysts for carbon-heteroatom bond formation
(Massachusetts Institute of Technology, 2015)
The research presented in this dissertation is aimed at the development of novel methodologies for carbon-heteroatom cross-coupling reactions catalyzed by late-transition metals. Both palladium and copper are central to ...
The nickel-catalyzed Mizoroki-Heck reaction : high regioselectivity in Olefin migratory insertion and photoredox-enabled indoline formation
(Massachusetts Institute of Technology, 2015)
[chemical formula and color illustrations ...] Achieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were ...
Development of new transition metal catalysts for C-N bond formation and continuous flow processes for C-F bond formation
(Massachusetts Institute of Technology, 2015)
The work presented in this dissertation addresses the development of new methodologies and processes to form carbon-nitrogen (C-N) and carbon-fluorine (C-F) bonds. The development of methods for the formation of C-N and ...
Total synthesis of cyclotryptamine and diketopiperazine alkaloids and biosynthetic pathway investigation of unsymmetrical diketopiperazine dimers
(Massachusetts Institute of Technology, 2018)
I. Total Synthesis of (-)-Hodgkinsine, (-)-Calycosidine, (-)-Hodgkinsine B, (-)-Quadrigemine C and (-)-Psycholeine The enantioselective total synthesis of (-)-hodgkinsine, (-)-calycosidine, (-)-hodgkinsine B, (-)- quadrigemine ...
Rational design of polymer networks and bottlebrush block copolymers
(Massachusetts Institute of Technology, 2017)
Chapter 1: Introduction to Polymer Networks and Bottlebrush Block Copolymers We introduce polymer networks and the contribution of this author's thesis in the context of new polymer gel design and analysis of topological ...
Photoredox activation of SF₆ for fluorination, on-demand automated titration of organometallic reagents in continuous flow, and progress toward an enantioselective synthesis of bedaquiline
(Massachusetts Institute of Technology, 2017)
Chapter 1: Photoredox Activation of SF₆ for Fluorination [chemical formula] We report the first practical use of SF₆ as a fluorinating reagent in organic synthesis. Photoredox catalysis enables the in situ conversion of ...
Development of new catalytic transformations and reagents for the construction of C-N and C-S bonds
(Massachusetts Institute of Technology, 2015)
Chapter 1. Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Triflates with Sodium Cyanate: A Practical Synthesis of Unsymmetrical Ureas. An efficient method for palladium-catalyzed cross-coupling of aryl chlorides ...
Chiral phosphine-catalyzed asymmetric transformations of allenoates and alkynoates and photoinduced, copper-catalyzed C-N couplings with aromatic nitrogen ceterocycles
(Massachusetts Institute of Technology, 2015)
Chapter 1 describes the development of chiral biphenyl-derived phosphepines and their application as catalysts for an asymmetric [4 + 1] annulation to form functionalized cyclopentenes bearing a non-spirocyclic quaternary ...