Themed collection Celebrating the 75th Birthday of Professor Barry Trost

This special issue is dedicated to Barry M. Trost, Tamaki Professor of Humanities and Sciences, on the occasion of his 75th birthday.

Honoring the 75th Birthday of Barry M. Trost.

Recent advances in ruthenium-catalysed hydrosilylation of C–C multiple bonds and its application to organic synthesis are highlighted.

This review covers new developments in the transition metal-catalyzed allylic alkylations of non-stabilized enolates, preferentially generated from ketone, esters or amides.

Non-heteroatom-stabilized group 6 metal carbene complexes: versatile reagents or intermediates in stoichiometric or catalytic reactions in organic synthesis.

This review covers the recent studies featuring the development of catalysts for alkene hydroaminomethylation.

With the advent of directed evolution of stereoselective enzymes almost 20 years ago and the rapid development of this exciting area of research, the traditional limitations of biocatalysts in organic chemistry have been eliminated.

Donor–acceptor (DA) cyclopropanes are extensively studied and well established as building blocks for the synthesis of highly substituted carbo- and heterocyclic compounds. Despite of similar ring strain, the homologous DA cyclobutanes were long ignored. This personal account details our group's research towards the application of DA cyclobutanes in cycloaddition chemistry.

This review covers chirality transfer in metal-catalysed intermolecular addition reactions involving allenes, including axial-to-central chirality transfer, asymmetric catalysis and racemization.

The synthesis, some of the properties and the applications of fluorous phosphines in biphasic, organometallic and organo-catalysis were reviewed.

A highly efficient synthesis of the DEFG-ring system of rubriflordilactone B via polar-radical-crossover cycloaddition and carbonyl allylation/lactonization is described.

A simple and efficient method for conversion of 2-iodo/2-nitro benzoic acids and dihydropyranone-fused benzoic acids into corresponding anilines, using tosyl azide, under transition metal-free conditions was developed. Steric and electronic effects play crucial role.

The formation of structurally differentiated indolizidinones is guided by a diverse behaviour of spirocyclopropaneisoxazolidine precursors under fluorination reactions.

Trifluoromethyl-substituted α-allenols are cyclized to the corresponding 2,5-dihydrofurans in the presence of neutral or cationic gold catalysts.

A highly efficient manganese-catalysed hydroperoxidation of carbon–carbon double bonds of enynes as well as styrene derivatives using N-hydroxyphthalimide, N-hydroxybenzotriazole or N-hydroxysuccinimide was developed.

The present work describes the unprecedented use of Fluoroalkyl Amino Reagents (FARs) to afford 2,4-bis(fluoroalkyl)-substituted quinoline derivatives in two steps under mild reaction conditions, in good yields and with a very good regioselectivity.

Polypropionates are synthesized using a combination of a copper-catalyzed asymmetric allylic alkylation, ruthenium-catalyzed cross-metathesis and iridium-catalyzed asymmetric allylic etherification.

A new Pd-catalyzed alkene carboalkoxylation strategy for the preparation of 2,3-dihydrobenzofurans is described.

The synthesis of highly functionalized 16,17,18-trinortaxane analogues based on a dienyne cyclization is described.

A resorcin[6]arene cavitand bearing sulfate bridges is herein reported. The host is able to interact with ammonium guests through the sulfate bridges.

A significant effect of the linker was observed on association chirality during the interpenetrative dimeric association of clothespin-shaped Pd complexes bearing either rigid or flexible linkers.

We describe the iron-catalyzed reductive cleavage of N–O-bonds in oxazines using malononitrile as reductant, which – in sequence with a [4 + 2]-cycloaddition – can be considered as an efficient way for the diastereoselective 1,4-aminohydroxylation of 1,3-dienes.

The oxidant–base bifunctionality of DEAD realized highly reliable cross dehydrogenative coupling of tetrahydroisoquinoline derivatives via aminal intermediates.

Switching between the intermolecular reaction and the intramolecular reaction was achieved at will using flow microreactors.

Careful consideration of the chemical mechanism for an oxidative condensation reaction led to improved current flow for the electrolysis.

Platinum- and iridium-catalyzed cycloisomerizations of 1,6 enynes that proceed via a C–C bond migration into a carbenoid intermediate are described.

Catalytic asymmetric 1,4-addition reactions of simple esters have been developed. The desired reactions proceeded smoothly with high enantioselectivities.

A new type of phosphoramidite-thioether ligand has been developed for Pd-catalysed asymmetric C-3 allylic alkylation of indoles with excellent yields and enantioselectivities.

A P-chiral P,π-hybrid ligand was applied to the asymmetric conjugate addition of aryl boronic acids to β-substituted nitroalkenes.

A convenient synthetic route to 2,3-diarylbenzo[b]thiophene derivatives via Ag-catalyzed intermolecular oxidative cyclization between bench-stable N-arylthio succinimides and unactivated internal alkynes is demonstrated herein.

An iterative asymmetric hydration of dienoates approach to Leucasndrolide A was explored.

A series of tetraphenylethene derivatives with through-space conjugation and aggregation-enhanced emission properties are synthesized and studied.

The diastereo- and enantioselective synthesis of cyclohexanone-fused spirospyrazolones through an asymmetric Michael/Michael/aldol cascade reaction catalyzed by squaramide and diphenylprolinol silyl ether, followed by a sequential oxidation was developed.

The asymmetric total synthesis of the optically pure catunaregin was accomplished in 7 steps from a known methyl ester using an asymmetric syn-selective aldol reaction and the successive ketalization of a furan diol derivative under acidic conditions.

Complementary diastereoselectivity for C–H and C–C bond formation, in para disposition, leading to one indenonaphthacene derivative: proton versus potassium assistance.

The synthesis of 3-aryl-3-hydroxy-2-oxindoles, which are a structural motif found in various natural products and pharmaceutically active compounds, was conducted via reductive coupling of (2-aminophenyl)(aryl)methanone derivatives and CO₂ as a key step. The conditions employing Mg with chlorotrimethylsilane in DMA are the best for the reductive coupling. The reductive coupling and acid-catalyzed lactam formation can be performed in a one-pot reaction to give the oxindoles.

The annulation of 1-cinnamyloxy-2-ethynylbenzene derivatives using a hydrazone–palladium catalyst system proceeded smoothly and gave the corresponding 2-substituted-3-cinnamylbenzofurans in good-to-excellent yields.

A versatile cascade route to cyclic imides via direct functionalization of the β-alkenyl C–H bond of alkenoic acids was developed.

A series of unsymmetrical palladacycles have been synthesised and evaluated as catalysts in aldol and vinyl epoxide coupling chemistry.

A Sandmeyer type process is disclosed that allows the straightforward synthesis of pentafluoroethyl thioethers from aromatic amines and tetramethylammonium pentafluoroethylthiolate.

A supramolecular polyrotaxane constructed by pillar[5]arene-based pseudo[2]rotaxanes via the incorporation of metal–ligand coordination could further self-assemble to form a stimuli-responsive supramolecular gel at high concentration.

The formation of chelated ruthenium alkylidenes with the oxygen of sulfonamides and acetates and their complexation with carbon monoxide have been studied.

4-(Hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3H)-ones are readily prepared in a one-pot fashion by a coupling–isomerization–elimination (CIE) sequence from N-Boc protected 1-aryl propargyl carbamates and acid chlorides.

2,5-Disubstituted pyrroles are synthesized by acceptorless dehydrogenative reaction of 1,2-aminoalcohols and secondary alcohols by Pt/carbon catalyst.

The first metal-free, initiator-free, and general photochemical perfluoroalkylation of a variety of N,N-dialkylhydrazones was developed at room temperature in the absence of any external photocatalyst.

Orthogonal removal of naphthylmethyl (NAP) and anomeric O-p-methoxyphenyl (PMP) ethers using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and cerium(IV) ammonium nitrate, respectively, is described.

Development of two novel oxa-[3 + 2] cycloaddition reactions of Achmatowicz products with 1,3-dicarbonyl compounds for rapid and highly efficient assembly of polycyclic furopyranones is described. Plausible mechanisms were proposed.

Enantioselective transfer hydrogenation of dibenzo-fused-azepine-diones: N-substituted dibenzo[b,e]azepin-6-11-dione was achieved by ruthenium catalysis in the presence of formic acid/triethylamine as a mild hydrogen source.

A K₂S₂O₈-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency.

Povarov-type chemistry gives ready access to 2-acylquinolines.

A novel gold-catalyzed tandem alkyne amination/intramolecular O–H insertion has been developed. A variety of [1,4]oxazino[3,2-c]isoquinolines are readily accessed under mild reaction conditions by utilizing this strategy, thereby providing an efficient and practical route for the construction of synthetically useful fused isoquinolines.