Jonathan Clayden

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Jonathan Paul Clayden
Born (1968-02-06) 6 February 1968 (age 56)
Kampala, Uganda
NationalityBritish
AwardsRoyal Society of Chemistry's Merck Prize
Royal Society of Chemistry's Stereochemistry Prize
Royal Society of Chemistry's Corday-Morgan Medal
Scientific career
Institutions University of Bristol
University of Manchester
University of Cambridge
Thesis The asymmetric epoxidation of allylic phosphine oxides: a stereocontrolled synthesis of allylic systems  (1993)
Doctoral advisor Stuart Warren
Website www.claydenchemistry.net

Jonathan Paul Clayden CChem FRSC (born 6 February 1968) is a Professor of organic chemistry at the University of Bristol.

Contents

Education

Whilst at secondary school, he represented the UK at the International Chemistry Olympiad in 1986, winning a bronze medal. In 1992 he obtained his PhD [1] at the University of Cambridge working with Dr Stuart Warren on asymmetric synthesis using phosphine oxide chemistry. He then carried out a postdoc with Prof Marc Julia and in 1994 became a lecturer in organic chemistry at the University of Manchester where he became a reader in 2000 and a Professor of Organic Chemistry in 2001. In 2015 he moved to a chair in chemistry at the University of Bristol.

Research

His research interests encompass various areas of synthesis and stereochemistry, particularly where conformation has a role to play: asymmetric synthesis, atropisomerism, [2] organolithium chemistry, remote stereochemical effects [3] and dynamic foldamer chemistry. [4] He is one of the authors of the organic chemistry textbook - Organic Chemistry by Clayden, Greeves, Warren and Wothers. [5] He also wrote Organolithiums: Selectivity for Synthesis, [6] which concerns the use of organolithium compounds in organic synthetic reactions.

From 2005 to 2011 he was editor-in-chief of the Open Access Beilstein Journal of Organic Chemistry.

Related Research Articles

<span class="mw-page-title-main">Atropisomer</span> Stereoisomerism due to hindered rotation

Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual conformers. They occur naturally and are important in pharmaceutical design. When the substituents are achiral, these conformers are enantiomers (atropoenantiomers), showing axial chirality; otherwise they are diastereomers (atropodiastereomers).

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular H2. It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular H2 used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis. It uses hydrogen donor compounds such as formic acid, isopropanol or dihydroanthracene, dehydrogenating them to CO2, acetone, or anthracene respectively. Often, the donor molecules also function as solvents for the reaction. A large scale application of transfer hydrogenation is coal liquefaction using "donor solvents" such as tetralin.

In organosilicon chemistry, silyl enol ethers are a class of organic compounds that share the common functional group R3Si−O−CR=CR2, composed of an enolate bonded to a silane through its oxygen end and an ethene group as its carbon end. They are important intermediates in organic synthesis.

The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.

Eric N. Jacobsen is the Sheldon Emery Professor of Chemistry and former chair of the department of chemistry and chemical biology at Harvard University. He is a prominent figure in the field of organic chemistry and is best known for the development of the Jacobsen epoxidation and other work in selective catalysis.

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information to transfer from one molecule to the target, forming the product as a single enantiomer. The chiral information is most commonly contained in a catalyst and, in this case, the information in a single molecule of catalyst may be transferred to many substrate molecules, amplifying the amount of chiral information present. Similar processes occur in nature, where a chiral molecule like an enzyme can catalyse the introduction of a chiral centre to give a product as a single enantiomer, such as amino acids, that a cell needs to function. By imitating this process, chemists can generate many novel synthetic molecules that interact with biological systems in specific ways, leading to new pharmaceutical agents and agrochemicals. The importance of asymmetric hydrogenation in both academia and industry contributed to two of its pioneers — William Standish Knowles and Ryōji Noyori — being collectively awarded one half of the 2001 Nobel Prize in Chemistry.

Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry.

In chemistry, metal-catalysed hydroboration is a reaction used in organic synthesis. It is one of several examples of homogeneous catalysis.

In organic chemistry, carbonyl allylation describes methods for adding an allyl anion to an aldehyde or ketone to produce a homoallylic alcohol. The carbonyl allylation was first reported in 1876 by Alexander Zaitsev and employed an allylzinc reagent.

Radical fluorination is a type of fluorination reaction, complementary to nucleophilic and electrophilic approaches. It involves the reaction of an independently generated carbon-centered radical with an atomic fluorine source and yields an organofluorine compound.

Dialkylbiaryl phosphine ligands are phosphine ligands that are used in homogeneous catalysis. They have proved useful in Buchwald-Hartwig amination and etherification reactions as well as Negishi cross-coupling, Suzuki-Miyaura cross-coupling, and related reactions. In addition to these Pd-based processes, their use has also been extended to transformations catalyzed by nickel, gold, silver, copper, rhodium, and ruthenium, among other transition metals.

Cobalt(II)–porphyrin catalysis is a process in which a Co(II) porphyrin complex acts as a catalyst, inducing and accelerating a chemical reaction.

The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an olefin by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen to produce an alcohol with Markovnikov selectivity.

Corinna S. Schindler is a Professor of Chemistry at the University of Michigan. She develops catalytic reactions with environmentally benign metals such as iron, towards the synthesis of biologically active small molecules. For her research in the development of new catalysts, Schindler has been honored with several early-career researcher awards including the David and Lucile Packard Foundation Fellowship in 2016, the Alfred P. Sloan Fellowship in 2017, and being named a member of the C&EN Talented 12 in 2017. Schindler has served on the Editorial Board of Organic and Bimolecular Chemistry since 2018.

Paul Knochel is a French chemist and a member of the French Academy of Sciences.

<span class="mw-page-title-main">Nontrigonal pnictogen compounds</span>

Nontrigonal pnictogen compounds refer to tricoordinate trivalent pnictogen compounds that are not of typical trigonal pyramidal molecular geometry. By virtue of their geometric constraint, these compounds exhibit distinct electronic structures and reactivities, which bestow on them potential to provide unique nonmetal platforms for bond cleavage reactions.

Tsutomu Katsuki was an organic chemist who primarily focused on asymmetric oxidation reactions utilizing transition metal catalysts.

<span class="mw-page-title-main">Zhu Jieping</span> French chemist specialized in total synthesis

Jieping Zhu is an organic chemist specializing in natural product total synthesis and organometallics. He is a professor of chemistry at EPFL and the head of the Laboratory of Synthesis and Natural Products.

<span class="mw-page-title-main">Tetraethylammonium trichloride</span> Chemical compound

Tetraethylammonium trichloride (also known as Mioskowski reagent) is a chemical compound with the formula [NEt4][Cl3] consisting of a tetraethylammonium cation and a trichloride as anion. The trichloride is also known as trichlorine monoanion representing one of the simplest polychlorine anions. Tetraethylammonium trichloride is used as reagent for chlorinations and oxidation reactions.

Copper-catalyzed allylic substitutions are chemical reactions with unique regioselectivity compared to other transition-metal-catalyzed allylic substitutions such as the Tsuji-Trost reaction. They involve copper catalysts and "hard" carbon nucleophiles. The mechanism of copper-catalyzed allylic substitutions involves the coordination of copper to the olefin, oxidative addition and reductive elimination. Enantioselective versions of these reactions have been used in the synthesis of complex molecules, such as (R)-(-)-sporochnol and (S)-(-)-zearalenone.

References

  1. Clayden, Jonathan (1993). The asymmetric epoxidation of allylic phosphine oxides: a stereocontrolled synthesis of allylic systems (PhD thesis). University of Cambridge.
  2. Clayden, Jonathan; Moran, Wesley J.; Edwards, Paul J.; LaPlante, Steven R. (17 August 2009). "The Challenge of Atropisomerism in Drug Discovery". Angewandte Chemie International Edition. 48 (35): 6398–6401. doi:10.1002/anie.200901719. ISSN   1521-3773. PMID   19637174.
  3. Byrne, Liam; Solà, Jordi; Boddaert, Thomas; Marcelli, Tommaso; Adams, Ralph W.; Morris, Gareth A.; Clayden, Jonathan (3 January 2014). "Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction" (PDF). Angewandte Chemie International Edition. 53 (1): 151–155. doi:10.1002/anie.201308264. ISSN   1521-3773. PMID   24375739.
  4. Le Bailly, Bryden A. F.; Clayden, Jonathan (24 March 2016). "Dynamic foldamer chemistry". Chem. Commun. 52 (27): 4852–4863. doi: 10.1039/c6cc00788k . hdl: 1983/8e0ce263-cb79-455f-b99e-40f2db2b8ba5 . PMID   26955864.
  5. Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). Organic Chemistry (Second ed.). Oxford: OUP. ISBN   978-0-19-927029-3.
  6. Clayden, Jonathan (2002). Organolithiums: Selectivity for Synthesis. Oxford: Pergamon. ISBN   978-0-08-043261-8.