Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• organoboron substrates 31, including -B(OH)2, -Bpin, -BF3K, and -Bneo (neopentyl borate) derivatives noted as “-[B]” in Scheme 11, to produce aliphatic alcohols and phenols 32 with moderate to excellent yields. The versatility of this method is highlighted by the broad substrate scope of more than 50 examples

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

• Zi-Ying Xiao,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

• used in the reaction, a direct Michael addition of the arylamine to the C=C bond of the maleimide unit and sequential elimination of carbon dioxide and tert-butoxide ion gives the intermediate B, which in turn undergoes an allylic rearrangement to afford the product 5. In this process, no extra

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• analysis was obtained by slow evaporation of a diethyl ether/n-hexane solution, enabling its unambiguous structural determination by single-crystal X-ray diffraction (Figure 1). The planar BPP core and the isopropyloxy group on the zigzag edge are clearly visualized (Figure 1a and b). In a unit cell

• BPP-OiPr 3: a) top view, b) side view (thermal ellipsoids shown at 50% probability), and c) molecular packing of 3 in a unit cell. All the hydrogen atoms are omitted for clarity. a) UV–vis absorption spectra of BPP 2, BPP-OiPr 3, and BPP-dione 4 measured in toluene. Inset: magnified spectra of 2 and 3

• for the better visualization of the longest-wavelength peaks, b) normalized PL spectra of BPP 2, BPP-OiPr 3, and BPP-dione 4 measured in toluene with a 360 nm excitation. Inset: absolute PLQY of BPP 2 (excitation at 360 nm), BPP-OiPr 3 (excitation at 380 nm), BPP-dione 4 (excitation at 470 nm) in

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• -4,4a,5,7a-tetrahydrocyclopenta[b]pyran-3-yl)methanone (9). From 1,3-diphenylpropane-1,3-dione (224 mg, 1.0 mmol), ʟ-proline (6 mg, 0.05 mmol) and cyclopentadiene (330 mg, 5.0 mmol), compounds 8 (136 mg, 45%) and 9 (97 mg, 32%) were obtained as white crystalline solids. Major isomer 8 1H NMR (400 MHz

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

• Zhenlei Zhang,
• Ying Wang,
• Xingxing Pan,
• Manqi Zhang,
• Wei Zhao,
• Meng Li and
• Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

• model reaction was proposed (Scheme 6). First, 1a was acidified to form p-methylbenzenesulfinic acid A, and A was reduced by HI to form p-tolyl hypoiodothioite B, which then reacted with A to form the thiosulfonate C. 3a undergoes a cyclization reaction to form 3aa in an acidic environment. Compound B

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• Information File 1. The photochromic properties of N3, N4, and I1–I4 were investigated in n-hexane. Figure 1a,b and Figure S1 in Supporting Information File 1 show the absorption spectral changes of N3, N4, and I1–I4 in n-hexane upon UV light irradiation. Compounds N3(o), N4(o), and I1(o)–I4(o) have

• -methylbenzo[b]furan-3-yl)perfluorocyclopentene (N4). Compound N4 was synthesized in a manner similar to a procedure from [56]. 5-Methylthiazole (0.20 g, 2.1 mmol) was dissolved in anhydrous THF (30 mL) under argon atmosphere. A 1.6 M n-BuLi hexane solution (1.4 mL, 2.3 mmol) was slowly added dropwise to the

• 140.6, 143.2, 155.8, 171.2; HRMS–DART+ (m/z): [M + H]+ calcd for C19H13F6N2S2+, 447.0424; found, 447.0430. 1-(5-Methylthiazol-2-yl)-2-(3-methylbenzo[b]thiophen-2-yl)perfluorocyclopentene (I3). Compound I3 was synthesized in a manner similar to a procedure from [56]. 5-Methylthiazole (0.36 g, 3.6 mmol

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• exchange between PIDA and CF2HCOOH would generate PhI(OCOCF2H)2 A. Homolysis of A under visible light (72 W white light) produced an iodanyl radical B and a CF2H radical. The CF2H radical regioselectively added to 1a to form intermediate C. Subsequently, intermediate C could be converted into the radical

• intermediate D via intramolecular radical cyclization. A single-electron-transfer (SET) process then occurred between the radical B and the radical D, resulting in the generation of cationic intermediate E, difluoroacetate anion and PhI. Finally, the product 3a was obtained after the deprotonation by

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

• Asahi Kanno,
• Ryo Tanifuji,
• Satoshi Yoshida,
• Sota Sato,
• Saori Maki-Yonekura,
• Kiyofumi Takaba,
• Jungmin Kang,
• Kensuke Tono,
• Koji Yonekura and
• Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

• the natural product, cyanosafracin B (4), bearing a para-quinone moiety at the left end [14]. Considering the relationships between the aromatic ring structures and DNA alkylating ability, we envisioned a modular and flexibly modifiable synthetic approach that would allow for the initial installation

• reaction involves an in situ generation of the iminium cation A followed by isomerization to the thermodynamically more stable iminium cation B. Subsequent nucleophilic attack of a copper acetylide enabled regioselective C–C bond formation at the C11 position. After removal of the cyclic acetal, the

• , excited at 375 nm): 0.07 (c = 10 μM). Emission image was captured under UV light (365 nm, c = 100 μM in CHCl3). Strategies for the construction of the pentacyclic core scaffold of saframycin A (1). (a) Biosynthetic machinery catalyzed by an NRPS module SfmC. (b) Total syntheses utilizing the Pictet

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• anthranilic acid and B) access to heteroannulated pyrimidones by MCRs of suitably substituted heterocycles and formamide as C1 source. Access to the key building blocks 2–4 by employing three different nonisocyanide-based MCRs. Diversity and complexity were the essential features of our library of starting

Quantifying the ability of the CF₂H group as a hydrogen bond donor

• Matthew E. Paolella,
• Daniel S. Honeycutt,
• Bradley M. Lipka,
• Jacob M. Goldberg and
• Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

• HB complex. Values for ΔGcalc were then calculated as the weighted average of the free energy of each HB complex as in which PMe3PO···HB,a and PMe3PO···HB,b are the percent populations of the HB complex of Me3PO with the donor conformer a and b, respectively; PMe3PO | HB,a and PMe3PO | HB,b are the

• species, the counteranion is BF4−. The reference HB donors are in the dashed line box. Hydrogen bond donation ability determined by UV–vis spectroscopy titration. A) Formation of HB complexes of Reichardt's dye and HB donors. B) Kd values of Reichardt's dye–hydrogen bond donor complexes. For all cationic

• species, the counteranion is BF4−. C) Possible interactions that interfere with the titration outcomes. A) HB complex formation between a donor and tri-n-butylphosphine oxide. B) 1H NMR spectra of 2b (5.0 mM) in the presence of different concentrations of tri-n-butylphosphine oxide in anhydrous CD3CN at

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• strict 2:2 molar ratio (Figure 3), providing convincing evidence for the dimerization process. The complex crystallized in the monoclinic P2(1)/c space group with lattice constants a = 24.434(4) Å, b = 20.026(3) Å, and c = 23.779(4) Å. The dimeric superstructure was stabilized by multiple cooperative

• 2444.3405, respectively. Stacked 1H NMR spectra (CDCl3/CD3CN 1:1, v/v, 400 MHz, 298 K) of G1 upon addition of different equiv of H1 ([G1] = 1.0⋅10−3 M). (a) 0.0 equiv, (b) 0.2 equiv, (c) 0.4 equiv, (d) 0.6 equiv, (e) 0.8 equiv, (f) 1.0 equiv, (g) 1.2 equiv, (h) 1.4 equiv, and (i) only H1. Single-crystal X

• -ray structure of the complex H2 ⊃ G1. a) Dimeric structure formed by cyclo[6]aramide H2 and cationic guest G1, with each guest molecule threading one molecule of H2 at its end. b) A portion of the dimeric structure showing an array of hydrogen bonding interactions between the amide oxygen atoms of H2

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

• Takeshi Fujita,
• Haruna Yabuki,
• Ryutaro Morioka,
• Kohei Fuchibe and
• Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

• are generated by treating 1,1-difluoroethylenes with a zirconocene equivalent (ZrCp2, Scheme 1a) [8]. The resulting 1-fluorovinylzirconocenes B then undergo palladium-catalyzed coupling with aryl iodides to produce arylated fluoroethylenes. Additionally, (ii) we observed that electron-deficient 2

• activation of aromatic C–F bonds. Results and Discussion First, we explored optimal conditions for nickel-catalyzed defluorinative coupling using 2-fluoronaphtho[2,1-b]furan (1b) and m-tolylboronic acid (2b) as model substrates (Table 1). When 1b was reacted with 2b at 80 °C using Ni(cod)2 (10 mol %) as a

• -dimethoxyphenylboronic acid (2e), which has electron-withdrawing groups on the aromatic ring, also yielded a satisfactory result of 73%. Additionally, using 2-fluoronaphtho[2,1-b]furan (1b), the reaction with phenylboronic acid (2a) and arylboronic acids with a methyl group at the 3-position (2b) or a tert-butyl group

Cu(OTf)₂-catalyzed multicomponent reactions

• Sara Colombo,
• Camilla Loro,
• Egle M. Beccalli,
• Gianluigi Broggini and
• Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

• presence of catalytic amounts of Cu(OTf)2 lead to the formation of the products through formation of one C–C bond and three C–N bonds (Scheme 26) [44]. The same procedure allows a more general scope, giving access to imidazo[1,2-a]pyrimidine, imidazo[1,2-a]pyrazine and imidazo[2,1-b]thiazole derivatives

• the C=S bond. The subsequent elimination of H2S afforded the final product (Scheme 30) [48]. Analogously, piperazinylthiazoloquinolines 40 and thiazolocoumarins 41 were obtained using piperazine or piperidine, CS2 and substituted quinolines or coumarins [49]. The synthesis of furo[3,4-b]pyrazolo[4,3-f

• Michael-type addition of 5-aminoindazole to afford the first coupling product XXXVIII. The subsequent intramolecular amination and dehydration then leads to the final product (Scheme 31) [50]. Polycyclic spiroindoline-3,4’-pyrano[3,2-b]pyran-4-ones 43 were synthesized exploiting the three-component

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• structural motifs [13][14][15][16][17]. Remarkably, these compounds are not limited to the C(sp2)–C(sp2) axis, but new developments in the formation of C–N, C–B, or even N–N stereogenic axes have been achieved. To help the research community distill and abstract the relevant new knowledge, this review has

• prochiral 2-aryloxyisophthalaldehydes 57a,b with a range of aliphatic and aromatic alcohols 58a–g, as well as heteroaromatic amines 60 (Scheme 19). Chiral diaryl ethers of this type received increased attention lately. Biju, Gao, Zhang, and Zeng groups all reported high degrees of yields and

Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• formation. b) Transition (30 s): formation of a vesicle with a dent and stomatocytes. c) Further shape transition (60 s): to a wide-open stomatocyte. d) Final (120 s, angle 35°): shape evolved into a disk after 120 s before quenching. The temperature-dependent behavior of vesicles and shape Transformation

• : a) Thermograph of PBLG-PSar: Showing dehydration with a peak around 70 °C. b) The fluorescent intensity of pyrene measured at 376.6 nm divided by the intensity at 387.6 nm tracked over temperatures between 20 °C and 80 °C. c) DLS measurement: demonstrating a slight decrease in hydrodynamic radius of

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

• Laura D’Andrea and
• Simon Jademyr

Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4

• ), N,N-diphenethylhydroxylamine (b) as second product is proposed. The latter may be produced from the reaction of 2-phenylacetaldehyde (e) and the reduced amino product d via reductive alkylation [38][39][40] (Scheme 3). Further research is required to clarify the formation of high molecular weight

• mm, 1.7 µm) operated at 40 °C, using a linear gradient of the binary solvent system of buffer A (Milli-Q H2O/MeCN/formic acid, 95:5:0.1 v/v) to buffer B (MeCN/formic acid, 100:0.1 v/v) from 0 to 100% B in 3.5 min, then 1 min at 100% B, flow rate: 0.8 mL/min. Data acquisition was controlled by

• . Proposed mechanism for the formation of the hydroxylamine side product b. N-Phenethylhydroxylamine (d), originated during the reduction process, reacts with the acetaldehyde e resulting from the hydrolysis of the aldoxime precursor c. The reduced β-nitrostyrene scaffolds with their corresponding products

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• crystallography. Structures of compounds 1–3 and the polycyclic skeleton of 1 as mapped on a carbon schwarzite unit cell. (a) Structures of 1 in the colorless crystal; (b) structures of (P,M,P)-1 in the yellow crystal. (Carbon atoms are shown as ellipsoids at 50% probability level, in and H atoms are removed for

• nm) of compound 3 in cyclohexane (1 × 10−5 mol/L). a) Synthesis of 1; b) reactions of 1; c) synthesis of 3. Supporting Information Supporting Information File 63: Experimental details, characterization data, and spectra. Supporting Information File 64: CIF-files of compounds 1 and 3

Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• % yield over 2 steps) [34]. Upon exposure to NaNO2/HCl, diamine 3 was transformed into a diazonium salt, which was captured by KI to deliver the diiodide 4. Treatment of 4 with n-BuLi, PhPCl2, and H2O2 sequentially gave 2,8-difluoro-5-phenylbenzo[b]phosphindole 5-oxide (5) in 68% yield. With compound 5 in

• delight, by treatment of 5 with substituted carbazoles 6 in the presence of Cs2CO3 (5.0 equiv) in DMF at 100 °C, seven 2,8-bis(9H-carbazol-9-yl)-5-phenylbenzo[b]phosphindole 5-oxide derivatives 7 were furnished in good to excellent yields (77–91%). The structural characterization of the obtained molecules

• ORTEP drawing obtained using the X-ray crystallographic data of 7-H. (a) UV–vis absorption spectra of the PhFlOP-based emitters 7 measured at a concentration of ≈10−5 M in toluene at room temperature. (b) UV–vis absorption spectra of 7-H measured at a concentration of ≈10−4 M in different solvents at

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• -diiodonaphthalene (12) and thiophene-3-ylboronic acid and ester derivatives 17 under the optimized conditions reported in our previous work (Table 1) [43]. Gratifyingly, the reaction worked smoothly with the use of thiophene-3-ylboronic acid (17a) to give acenaphtho[1,2-b]thiophene (15a) in 76% yield when Pd(dppf

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• Beatriz Dedeiras Catarina S. Caldeira Jose C. Cunha Clara S. B. Gomes M. Manuel B. Marques LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, NOVA FCT , 2829-516 Caparica, Portugal 10.3762/bjoc.20.272 Abstract The reactivity of our recently disclosed hypervalent iodine

• Supporting Information File 1). We propose a mechanism pathway involving the retro-Michael addition of 4, releasing acrylate and hydrogen (H2). The charge of the sulfenate anion may shift between sulfur and oxygen atoms, possibly leading to an O-Michael addition (pathway B) [35]. The intermediate of these

Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation

• Perry van der Heide,
• Michele Retini,
• Fabiola Fanini,
• Giovanni Piersanti,
• Francesco Secci,
• Daniele Mazzarella,
• Timothy Noël and
• Alberto Luridiana

Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271

• slight increase in chemical yield. Giese reaction: Radical addition on olefins with an electron-withdrawing group (EWG) followed by a HAT or SET and protonation; halogen-atom transfer: (a) tin-mediated XAT, (b) XAT initiated by a photocatalyst (PC) and mediated by boranes (B), silanes (Si) or alkylamines

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• is the same for all triphenylene derivatives. Thus, compound F crystallizes in an orthorhombic crystallographic system (Pccn space group, no. 56) [50] with unit cell dimensions a = 13.2645(2) Å, b = 5.5284(1) Å, and c = 22.7571(3) Å; the unit cell contains 8 molecules, which gives a calculated

• rather flat, with, however, a substantial planar deviation of the pending perfluorophenyl group, forming a large tilt of ca. 45°. From the view along the b-axis, it can be seen that the flat triphenylene cores stack perfectly on top of each other, but with the pending fluoroarene group being alternately

• Supporting Information File 1 (Figure S36). Comparative bar graph summarizing the thermal behavior of Fn, BTP6, and PHn derivatives (2nd heating DSC data). Representative S/WAXS patterns of Fn and Gnm compounds. Absorption (a) and emission (b) spectra of F6 and G66, measured in different solvents at a

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• . Experimental Typical experimental procedure for the C–H arylation of pyridine derivative 5-octyldibenzo[b,f][1,7]naphthyridin-6(5H)-one (2a): To a screw-capped test tube equipped with a magnetic stirring bar were added amide 1a (44.1 mg, 0.100 mmol), potassium carbonate (42.0 mg, 0.304 mmol

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

• Sergio Torres-Oya and
• Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

• hydrogen bonding with the protonated tertiary amine. Then, a Michael addition of malononitrile to the azadiene takes place to obtain exclusively the (S)-intermediate A. Subsequently an intramolecular nucleophilic addition of the nitrile leads to the intermediate B, which undergoes tautomerization to

• the bifunctional squaramide enables a stereoselective Michael addition of the azlactone to the azadiene forming intermediate A which transforms into intermediate B, which then undergoes an intramolecular cyclization to give the desired product 20. In 2020, Ni, Song and co-workers described a

• the nitrogen atoms. Then, the azlactone enolate undergoes a nucleophilic attack on its Si-face via Mannich reaction with the 2-benzothiazolimine leading to intermediate A which evolves toward its resonance form B, responsible of the intramolecular attack of the negatively charged nitrogen to the