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Selective Oxidative Homo‐ and Cross‐Coupling of Phenols with Aerobic Catalysts.
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In this paper, simple catalysts that use atom-economical oxygen as the terminal oxidant to accomplish selective ortho-ortho, orthopara, or para-para homo-couplings of phenols are described.Abstract:
Simple catalysts that use atom-economical oxygen as the terminal oxidant to accomplish selective ortho–ortho, ortho–para, or para–para homo-couplings of phenols are described. In addition, chromium salen catalysts have been discovered as uniquely effective in the cross-coupling of different phenols with high chemo- and regioselectivity.read more
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Journal ArticleDOI
Scalable Access to Arylomycins via C–H Functionalization Logic
TL;DR: A simplified route predicated on simple C–H functionalization logic that is enabled by a Cu-mediated oxidative phenol coupling that mimics the putative biosynthesis is presented, which is the largest of its kind and can be easily performed on gram scale.
Asymmetric Oxidative Coupling of 2-Hydroxycarbazoles
TL;DR: The goal of the project is to use a chiral vanadium catalyst and oxygen to achieve high enantioselectivity in a more efficient oxidative coupling to form biscarbazoles.
Oxidative Coupling of Phenols
TL;DR: In this paper, the authors use the atom economical oxidant O2 and metal-based catalysts which mimic the active sites of the enzymes to bring about these transformations, which is a striking feature in many biosynthetic pathways.
Part A: Palladium(II)-catalyzed enantioselective Saucy-Marbet Claisen rearrangement of propargyloxy indoles to quaternary oxindoles and spirocyclic lactones. Part B: The regioselective oxidative coupling of phenols
Abstract: Part A. The first catalytic, enantioselective Saucy-Marbet Claisen rearrangement has been developed. Palladium(II) catalysts with BINAP or t-BuPHOX ligands were discovered as superior in catalyzing Claisen rearrangements of proparyloxy-substituted indoles to generate oxindoles bearing allenyl-substituted quaternary centers. Mechanistic evidence firmly established the intermediacy of a [3,3']-sigmatropic rearrangement vs ionic or stepwise processes. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation. Part B. The formation of biaryl C-C bonds by oxidative reactions is a well-recognized process in biological systems, being the second most common way nature constructs C-C bonds. However, very little progress has been made in the development of catalytic, regioselective methods for the oxidative coupling of phenols. High throughput experimentation (HTE) was used to screen a series of redox-active Salen and Salan metal complexes in the presence of O2. Copper, manganese, vanadium and ruthenium-catalyzed oxidative coupling conditions were developed that efficiently afford biaryls from a number of phenols with high yield and regioselectivity. Degree Type Dissertation Degree Name Doctor of Philosophy (PhD) Graduate Group Chemistry First Advisor Marisa C. Kozlowski
References
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Book
CRC Handbook of Chemistry and Physics
TL;DR: CRC handbook of chemistry and physics, CRC Handbook of Chemistry and Physics, CRC handbook as discussed by the authors, CRC Handbook for Chemistry and Physiology, CRC Handbook for Physics,
Journal ArticleDOI
Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.
Journal ArticleDOI
Metal–Salen Schiff base complexes in catalysis: practical aspects
TL;DR: Practical guidelines for the preparation and use of different Schiff base metal complexes in the field of catalytic transformations are discussed in this tutorial review.
Journal ArticleDOI
Atroposelective Synthesis of Axially Chiral Biaryl Compounds
Gerhard Bringmann,Anne J. Price Mortimer,Paul A. Keller,Mary J. Gresser,James Garner,Matthias Breuning +5 more
TL;DR: This Review classifies strategies in the asymmetric synthesis of axially chiral biaryl compounds according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications.
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Atroposelective total synthesis of axially chiral biaryl natural products.
TL;DR: Gerhard Bringmann's research interests focus on the field of analytical, synthetic, and computational natural product chemistry, i.e., on axially chiral biaryls, which is characterized by a broad structural diversity.
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