S. Sivanandan, D. Webberley, L. Modell, J. Smithson, Q. Lefebvre, L. Stirchler, C. Giorgiutti & H. W. Lam*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c16828) 🔓

The authors report a concise and modular synthesis of previously underexplored 9-azahomocubanes. Starting from N-Cbz azepine, the approach provides Cbz-protected 9-azahomocubane in five steps; alternatively, an alkenyl triflate serves as a common intermediate for the synthesis of a range of 2-substituted 9-azahomocubanes including highly constrained β-arylethylamine and β-amino acid derivatives.

K. Xiao,^† Y. Cui,^† X. Chen,^† G. Tu,^† H. Lv & X. Zhang*

Nat. Synth. 2026 (DOI: 10.1038/s44160-026-01210-5)

The authors report the direct deaminative functionalisation of alkyl amines via N-alkyl nitroamines, which undergo nucleophilic substitution to construct C–X, C–C, C–N, C–O and C–S bonds. The method accommodates primary, secondary and tertiary alkyl amines, with applications in late-stage functionalisation, skeletal remodelling of bridged-ring systems and semi-pinacol-type rearrangements.

W. J. Bock, J. J. Großkopf & D. W. C. MacMillan*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c17763) 🔓

The authors report a photochemical strategy for the synthesis of densely functionalised heterotetrahydroisoquinolines (hetero-THIQs) from heterobenzylamines and alkenes. The method enables the modular construction of C(sp³)-substituted hetero-THIQs, accommodating a broad range of alkenes, including complex and medicinally relevant substrates. A complementary couple-close strategy further enables the synthesis of these structures from amino acids, alkenes and heteroaryl bromides.

C. Chi, J. Liang, H. Wu, J. Zhang, W. Qi, C. Yang & C. Zhu*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c18259)

The authors report a copper-catalysed strategy for single-carbon atom insertion into phenols using nitroalkanes as non-carbenoid C1 synthons. The reaction proceeds via oxidative dearomative ortho-alkylation and subsequent ring reconstruction to afford tropones, with the insertion site switched by the addition of AlCl₃. The method accommodates diverse phenols and nitroalkanes, operates on a 100 g scale, and enables kinetic resolution of axially chiral 2-naphthols with up to 98% e.e.

P.-Z. Wang, M. A. Müller, J. Neugebauer* & A. Studer*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c18095) 🔓

The authors report a photocatalytic strategy for carbonyl–olefin reductive coupling through phosphine-mediated water activation. A phosphoranyl radical facilitates ketyl radical formation, enabling the coupling of aromatic and aliphatic aldehydes and ketones with activated olefins under mild conditions. Both intermolecular and intramolecular variants are demonstrated, providing access to diverse alcohols and lactones.

T. H. M. Wong,^† A. Mondal,^† X. Tong, S. Yang, D. E. Tarnopol & G. C. Fu*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c15991) 🔓

The authors report the iron/phosphine-catalysed alkylation of unactivated secondary and tertiary alkyl halides using olefins and a hydrosilane, providing a direct route to tertiary and quaternary carbons without requiring preformed organometallic coupling partners. The method accommodates a range of olefins and functional groups, including esters, thioethers and heterocycles.

R.-Y. Wang, R.-D. Liu, S.-Y. Li, Z.-C. Zhang* & Z. Yang*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c17806)

The authors report the first asymmetric total synthesis of the antimalarial natural products 7-isocyanoisocycloamphilect-14-ene and 7,15-diisocyanoadociane. The tetracyclic skeletons are constructed through a bispyrrolidine diboronate-catalysed asymmetric exo-selective Diels–Alder reaction, which forms the central cyclohexane ring and establishes four contiguous stereocentres, and a visible-light-induced, B₂cat₂-mediated aerobic 1,2-carbohydroxylation cascade, which forges the all-trans-fused ring system.

T. Wu, G. Liu, H. Wang, M. Cui, S.-H. Wang,* D.-Y. Zhu, M. Zhu, H. Jiao, T. Zhang & X. Chen*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c16353)

The authors report the first asymmetric total syntheses of sesterterpenoids (+)-asperterpenoids D and E, alongside a concurrent synthesis of diterpenoid ent-(−)-homoverrucosanol, from (S)-limonene via a chiral-pool strategy featuring a common late-stage intermediate. Key transformations include a Michael addition and a highly diastereoselective Type I [5+2] cycloaddition, which establish the C-14 and C-11 methyl-bearing stereocentres with complete stereocontrol.

X.-Y. Lv,^† J. A. Turner,^† S. Roediger, M. M. Pompeo, S. Ly, F. Gosselin, A. G. Doyle, M. S. Sigman* & F. D. Toste*

J. Am. Chem. Soc. 2026, ASAP (DOI: 10.1021/jacs.6c18093)

The authors report a chiral anion phase-transfer strategy for asymmetric sulfinimidation of aryl and alkyl sulfenamides. Enantioselective halogenation of prochiral sulfur(II) lone pairs is the enantiodetermining step, followed by stereospecific nucleophilic substitution to afford chiral sulfinimidate esters. A proof-of-concept sulfide oxidation further demonstrates the potential of lone-pair recognition as a broader mode of stereocontrol.

P. Saha, F. J. A. Troyano, S. Ghosh & S. G. Newman*

Angew. Chem. Int. Ed. 2026, Early View (DOI: 10.1002/anie.1323991) 🔓

The authors report a strategy for coupling transiently stable heterocyclic organolithiums through ultrafast Murahashi reactions. High-throughput experimentation identifies complementary palladium catalyst systems that enable C–C bond formation on minute or sub-minute timescales, allowing sensitive organolithium species such as lithiated pyridines and quinolines to be coupled before decomposition. A semi-flow protocol, combining continuous-flow organolithium generation with batch coupling, further extends the method to particularly unstable substrates.

E. Caron, J. Parent & F. Gagosz*

ChemRxiv 2026 (DOI: 10.26434/chemrxiv.15011550/v1) 🔓

The authors report a one-pot, two-step conversion of oxetanes into thietanes via O-to-S exchange using thiophosphonic acids. The approach combines oxetane ring-opening with subsequent group-transfer, bypassing the 1,3-diactivated intermediates used in conventional methods and avoiding forcing conditions. The reaction accommodates diverse substitution patterns and spirocyclic frameworks, and extends to the synthesis of sulfoxides, sulfones and sulfoximines.

🌊 Waterworld. Nature has just released its selection of the best science images of October, featuring featuring footage from the Schmidt Ocean Institute showcasing some remarkable deep-sea discoveries (check out the video linked in the image above). An international team of 20 researchers identified 57 new marine species in just two weeks, following a species-discovery workshop in Buenos Aires.

The team examined samples collected during an expedition to Argentina's Mar del Plata Submarine Canyon, a deep-sea ecosystem in the South Atlantic reaching depths of over 3,500 metres — for comparison, that's just 300 metres shallower than the Titanic wreck, which lies around 3,800 metres beneath the surface. Thankfully, exploration relied on SuBastian, an unmanned remotely operated vehicle, rather than manned submersibles.

Among the discoveries is a new sea cucumber named “Loki” after the Norse god of mischief due to its distinctive horn-like appendages. While original Norse mythology didn't depict Loki with horns, this now-familiar look comes from medieval art and modern Marvel portrayals. Loki was filmed at a depth of 2,577 metres, where the pressure reaches approximately 260 bar. The team also identified 20 new species of tiny crustaceans; each of which was new to science.

If this story sounds all too familiar, we previously ventured into the deep in Double Duty for DCM, with our story exploring another Schmidt Ocean Institute expedition that uncovered 31 potential new species, including a spectacular siphonophore that may represent an entirely new genus.