Advanced search
Publication Cover
Future Medicinal Chemistry Volume 1, 2009 - Issue 5
Submit an article Journal homepage
189
Views
0
CrossRef citations to date
0
Altmetric
Research Article

New Preparation and Synthetic Reactions of 3,3,3-Trifluoropropynyllithium, -Borate and -Stannane: Facile Synthesis of Trifluoromethylated Allenes, Arylacetylenes and Enynes

Masaki Shimizu1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanCorrespondence[email protected]
View further author information
,
Masahiro Higashi1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Youhei Takeda1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Masahito Murai1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Guofang Jiang1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Yuiga Asai1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Yoshiaki Nakao1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
,
Eiji Shirakawa2 Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto666-8502, JapanView further author information
&
Tamejiro Hiyama1 Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto615-8510, JapanView further author information
 show all
Pages 921-945 | Published online: 19 Aug 2009

Bibliography

  • Hagmann WK . The many roles for fluorine in medicinal chemistry.J. Med. Chem.51(15), 4359–4369 (2008).
  • Kirk KL . Fluorination in medical chemistry: methods, strategies, and recent development.Org. Process Res. Dev.12(2), 305–321 (2008).
  • Müller K , FaehC, DiederichF. Fluorine in pharmaceuticals: looking beyond intuition.Science317(5846), 1881–1886 (2007).
  • Bégué JP , Bonnet-DelponD. Recent advances (1995–2005) in fluorinated pharmaceuticals based on natural products.J. Fluorine Chem.127(8), 992–1012 (2006).
  • Isanbor C , O‘HaganD. Fluorine in medicinal chemistry: a review of anti-cancer agents.J. Fluorine Chem.127(3), 303–319 (2006).
  • Kirk KL . Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules.J. Fluorine Chem.127(8), 1013–1029 (2006).
  • Special issue on fluorine in the life sciences. ChemBioChem5(5), 557–726 (2004).
  • Schlosser M . Introduction of fluorine into organic molecules: why and how.Tetrahedron34(1), 3–17 (1978).
  • Hiyama T . Organofluorine Compounds-Chemistry and Applications. Springer, Berlin, Germany (2000).
  • Smits R , CadicamoCD, BurgerK, KokschB. Synthetic strategies to α-trifluoromethyl and α-difluoromethyl substitute α-amino acids.Chem. Soc. Rev.37(8), 1727–1739 (2008).
  • Liu P , SharonA, ChuCK. Fluorinated nucleosides: synthesis and biological implication.J. Fluorine Chem.129(9), 743–766 (2008).
  • Romanenko VD , KukharVP. Fluorinated phosphonates: synthesis and biomedical application.Chem. Rev.106(9), 3868–3935 (2006).
  • Shimizu M , HiyamaT. Modern synthetic methods for fluorine-substituted target molecules.Angew. Chem. Int. Ed.44(2), 214–231 (2005).
  • Ma JA , CahardD. Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.Chem. Rev.104(12), 6119–6146 (2004).
  • Qiu XL , MengWD, QingFL. Synthesis of fluorinated amino acids.Tetrahedron60(32), 6711–6745 (2004).
  • Mikami K , ItohY, YamanakaM. Fluorinated carbonyl and olefinic compounds: basic character and asymmetric catalytic reactions.Chem. Rev.104(1), 1–16 (2004).
  • Lin P , JiangJ. Synthesis of monotrifluoromethyl-substituted saturated cycles.Tetrahedron56(23), 3635–3671 (2000).
  • Iseki K . Catalytic asymmetric synthesis of chiral fluoroorganic compounds.Tetrahedron54(46), 13887–13914 (1998).
  • Prakash GKS , YudinAK. Perfluoroalkylation with organosilicon reagents.Chem. Rev.97(3), 757–786 (1997).
  • Tozer MJ , HerpinTF. Methods for the synthesis of gem-difluoromethylene compounds. Tetrahedron52(26), 8619–8683 (1996).
  • McClinton MA , McClintonDA. Trifluoromethylations and related reactions in organic chemistry.Tetrahedron48(32), 6555–6666 (1992).
  • Bégué JP , Bonnet-DelponD. Preparation of trifluoromethyl ketones and related fluorinated ketones.Tetrahedron47(20–21), 3207–3258 (1991).
  • Bravo P , ResnatiG. Preparation and properties of chiral fluoroorganic compounds.Tetrahedron Asymmetry1(10), 661–692 (1990).
  • Welch JT . Advances in the preparation of biologically active organofluorine compounds.Tetrahedron43(14), 3123–3197 (1987).
  • Zanda M . Trifluoromethyl group: an effective xenobiotic function for peptide backbone modification.New J. Chem.28(12), 1401–1411 (2004).
  • Yoneda N , MatsuokaS, MiyauraN, FukuharaT, SuzukiA. Preparation of 1-aryl- or 1-alkenyl-2-(perfluoroalkyl)acetylenes.Bull. Chem. Soc. Jpn63(7), 2124–2126 (1990).
  • Konno T , ChaeJ, IshiharaT, YamanakaH. A first regioselective synthesis of 3-fluoroalkylated benzofurans via palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodophenol.Tetrahedron60(51), 11695–11700 (2004).
  • Chae J , KonnoT, IshiharaT, YamanakaH. A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes.Chem. Lett.33(3), 314–315 (2004).
  • Yamazaki T , MizutaniK, KitazumeT. Modified preparation method of trifluoromethylated propargylic alcohols and its application to chiral 2,6-dideoxy-6,6,6-trifluorosugars.J. Org. Chem.60(19), 6046–6056 (1995).
  • Hanamoto T , EgashiraM, IshizukaK, FurunoH, InanagaJ. Synthesis and reactions of 1-methyl-5-tributylstannyl-4-trifluoromethylpyrazole.Tetrahedron62(26), 6332–6338 (2006).
  • Hanamoto T , HakoshimaY, EgashiraM. Tributyl(3,3,3-trifluoro-1-propynyl)stannane as an efficient reagent for the preparation of various trifluoromethylated heterocyclic compounds.Tetrahedron Lett.45(41), 7573–7576 (2004).
  • Konno T , ChaeJH, MiyabeT, IshiharaT. Regioselective one-step synthesis of 4-fluoroalkylated isoquinolines via carbopalladation reaction of fluorine-containing alkynes.J. Org. Chem.70(24), 10172–10174 (2005).
  • Konno T , DaitohT, NoiriAet al. A highly regio- and stereoselective carbocupration of fluoroalkylated internal alkynes: a short total synthesis of the antiestrogenic drug panomifene. Org. Lett. 6(6), 933–936 (2004).
  • Konno T , DaitohT, NoiriAet al. Highly regio- and stereo-selective carbometallation reaction of fluorine-containing internal acetylenes with organocopper reagents. Tetrahedron 61(39), 9391–9404 (2005).
  • Borvendeg J . GYKI-13504.Drugs Future10(5), 395–396 (1985).
  • Borvendeg J , AnheuerZ. Influence of GYKI-13504, a new antioestrogen, on the responsiveness of isolated uterus removed from oestradiol pretreated rats to PGF(2α).Exp. Clin. Endocrino.86(3), 368–370 (1985).
  • Borvendeg J , HermannI, CsukaO. Antiestrogens, antiandrogens.Act. Phys. Hung.84(4), 405–406 (1996).
  • Erdelyi-Toth V , GyergyayF, SzamelIet al. Pharmacokinetics of panomifene in healthy volunteers at phase I/a study. Anticancer Drugs 8(6), 603–609 (1997).
  • Monostory K , JemnitzK, VereczkeyL, CziraG. Species differences in metabolism of panomifene, an analog of tamoxifen.Drug Met. Disp.25(12), 1370–1378 (1997).
  • Burton DJ , Yang Z-Y, Qiu W. Fluorinated ylides and related compounds. Chem. Rev.96(5), 1641–1715 (1996).
  • Burton DJ , YangZY, MorkenPA. Fluorinated organometallics: vinyl, alkynyl, allyl, benzyl, propargyl and aryl fluorinated organometallic reagents in organic synthesis.Tetrahedron50(10), 2993–3063 (1994).
  • Burton DJ , YangZY. Fluorinated organometallics: perfluoroalkyl and functionalized perfluoroalkyl organometallic reagents in organic synthesis.Tetrahedron48(2), 189–275 (1992).
  • Shimizu M , HigashiM, TakedaYet al. Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes. Synlett. (7), 1163–1165 (2007).
  • Shimizu M , JiangG, MuraiMet al. Facile synthesis of trifluoromethyl-substituted enynes: remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes. Chem. Lett. 34(12), 1700–1701 (2005).
  • Drakesmith FG , StewartOJ, TarrantP. The preparation and reactions of lithium derivatives of trifluoropropene and trifluoropropyne.J. Org. Chem.33(1), 280–285 (1968).
  • Katritzky AR , QiM, WellsAP. 2-Bromo-3,3,3-trifluoropropene: a facile trifluoromethylacetylene anion synthon.J. Fluorine Chem.80(2), 145–147 (1996).
  • Brisdon AK , CrossleyIR. Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry.Chem. Commun. (20), 2420–2421 (2002).
  • Konno T , ChaeJ, KandaMet al. Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives. Tetrahedron 59(38), 7571–7580 (2003).
  • Shimizu M , FujimotoT, LiuX, TakedaY, HiyamaT. Stereoselective preparation and cope rearrangement of 2-CF3-cis-2,3-bis(alkenyl)oxiranes: a facile route to 2-CF3-substituted oxacycles. Heterocycles76(1), 329–351 (2008).
  • Takeda Y , ShimizuM, HiyamaT. Straightforward synthesis of CF3-substituted triarylethenes by stereoselective threefold cross-coupling reactions. Angew. Chem. Int. Ed.46(45), 8659–8661 (2007).
  • Shimizu M , FujimotoT, LiuX, HiyamaT. A facile approach to 2-CF3-substituted seven-membered oxacycles via stereoselective preparation and cope rearrangement of 2-CF3- cis-2,3-bis(alkenyl)oxiranes. Chem. Lett.33(4), 438–439 (2004).
  • Liu X , ShimizuM, HiyamaT. A facile stereocontrolled approach to CF3-substituted triarylethenes: synthesis of panomifene. Angew. Chem. Int. Ed.43(7), 879–882 (2004).
  • Shimizu M , FujimotoT, LiuXet al. Stereoselective generation of cis-2-lithio-3-CF3-oxirane via CF3-substituted α-oxido carbenoids: highly stereoselective synthesis of CF3-substituted tri- and tetrasubstituted oxiranes and tetrasubstituted alkenes. Tetrahedron 59(49), 9811–9823 (2003).
  • Shimizu M , FujimotoT, MinezakiH, HataT, HiyamaT. New, general, and stereoselective synthesis of CF3-containing tri- and tetrasubstituted oxiranes and tetrasubstituted alkenes. J. Am. Chem. Soc.123(28), 6947–6948 (2001).
  • Bardin VV , AdoninNY, FrohnHJ.(Fluoroorgano)fluoroboranes and -borates. 14. Preparation of potassium ((perfluoroorgano)ethynyl)trifluoroborates K[RfC≡CBF3]. Organometallics24(22), 5311–5317 (2005).
  • Brisdon AK , CrossleyIR, PritchardRG, SadiqG, WarrenJE. Preparation and functionalization of a range of main-group trifluoropropynyl organometallic compounds: the application of metalloid-directed carbolithiation to the selective synthesis of novel fluorocarbon fragments.Organometallics22(26), 5534–5542 (2003).
  • Brummond KM , DeForrestJE. Synthesizing allenes today (1982–2006).Synthesis (6), 795–818 (2007).
  • Ma S . Some typical advances in the synthetic applications of allenes.Chem. Rev.105(7), 2829–2871 (2005).
  • Hashmi ASK . New and selective transition metal catalyzed reactions of allenes.Angew. Chem. Int. Ed.39(20), 3590–3593 (2000).
  • Zimmer R , DineshCU, NandananE, KhanFA. Palladium-catalyzed reactions of allenes.Chem. Rev.100(8), 3067–3125 (2000).
  • Hoffmann-Röder A , KrauseN. Synthesis and properties of allenic natural products and pharmaceuticals.Angew. Chem. Int. Ed.43(10), 1196–1216 (2004).
  • Dembitsky VM , MaokaT. Allenic and cumulenic lipids.Prog. Lipid Res.46(6), 328–375 (2007).
  • Yamazaki T , YamamotoT, IchiharaR. Preparation of CF3-containing 1,3-di- and 1,1,3-trisubstituted allenes. J. Org. Chem.71(16), 6251–6253 (2006).
  • Han HY , KimMS, SonJB, JeongIH. Novel synthesis of 1-aryl-1-trifluoromethylallenes.Tetrahedron Lett.47(2), 209–212 (2006).
  • Konno T , TanikawaM, IshiharaT, YamanakaH. Palladium-catalyzed coupling reaction of fluoroalkylated propargyl mesylates with organozinc reagents: novel synthesis of optically active fluorine-containing trisubstituted allenes.Chem. Lett.29(12), 1360–1361 (2000).
  • Burton DJ , HartgravesGA, HsuJ. A facile, general route to perfluoroalkyl allenes.Tetrahedron Lett.31(26), 3699–3702 (1990).
  • Hanzawa Y , KawagoeK, YamadaA, KobayashiY. Syntheses of trifluoromethylated diene derivatives through the Claisen rearrangement of trifluoromethylated propargylic and allylic alcohols.Tetrahedron Lett.26(2), 219–222 (1985).
  • Bosbury PWL , FieldsR, HaszeldineRN. Polyhalogenoallenes. Part 11. The preparation of some new perfluoro-1,2-dienes and their reactions with nucleophiles.J. Chem. Soc, Perkin Trans.1(5), 422–427 (1978).
  • Bosbury PWL , FieldsR, HaszeldineRN, MoranD. Polyhalogenoallenes. Part X. An improved preparation of perfluoro(3-methylbuta-1,2-diene) and the structure of its dimers.J. Chem. Soc. Perkin Trans.1, (11), 1173–1177 (1976).
  • Dolbier J r WR, Burkholder CR, Piedrahita CA. Fluorinated allenes: the syntheses of 1-fluoropropadiene, 1,1-difluoropropadiene and 1,1-difluoro-3-methyl-1,2-butadiene. J. Fluorine Chem.20(5), 637–647 (1982).
  • Burton DJ , HartgravesGA, HsuJ. A facile, general route to perfluoroalkyl allenes.Tetrahedron Lett.31(26), 3699–3702 (1990).
  • Hung MH . Fluorinated allenes and alkynes.Tetrahedron Lett.31(26), 3703–3706 (1990).
  • Shen Q , HammondGB. Regiospecific synthesis of bicyclo- and heterobicyclo-gem-difluorocyclobutenes using functionalized fluoroallenes and a novel Mo-catalyzed intramolecular [2 + 2] cycloaddition reaction. J. Am. Chem. Soc.124(23), 6534–6535 (2002).
  • Lentz D . Organometallic chemistry of fluorinated propadienes and butadienes.J. Fluorine Chem.125(6), 853–861 (2004)
  • Lentz D , WillemsenS. Fluorinated bis(enyl) ligands by metal-induced dimerization of fluorinated allenes.Angew. Chem. Int. Ed.40(11), 2087–2091 (2001).
  • Tsuji J , MandaiT. Palladium-catalyzed reactions of propargylic compounds in organic synthesis.Angew. Chem. Int. Ed. Engl.34(23–24), 2589–2612 (1996).
  • Ogasawara M , HayashiT. In: Modern Allene Chemistry. Krause N, Hashmi ASK (Eds). Wiley-VCH, Weinheim, Germany, 93–140 (2004).
  • Schwier T , SromekAW, YapDML, ChernyakD, GevorgyanV. Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.J. Am. Chem. Soc.129(32), 9868–9878 (2007).
  • Yamazaki T , HiraokaS, SakamotoJ, KitazumeT. Mesyloxy-group migration as the stereoselective preparation method of various functionalized olefins and its reaction mechanism.Org. Lett.3(5), 743–746 (2001).
  • Miyaura N , SuzukiA. Palladium-catalyzed cross-coupling reactions of organoboron compounds.Chem. Rev.95(7), 2457–2483 (1995).
  • Suzuki A . Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998.J. Organomet. Chem.576(1–2), 147–168 (1999).
  • Miyaura N . Cross-coupling reaction: a practical guide. In: Top. Curr. Chem. Miyaura N (Ed.). Springer-Verlag, Berlin, Germany, 11–59 (2002).
  • Darses S , GenetJP. Potassium organotrifluoroborates: new perspectives in organic synthesis.Chem. Rev.108(1), 288–325 (2008).
  • Stefani HA , CellaR, VieiraAS. Recent advances in organotrifluoroborates chemistry.Tetrahedron63(18), 3623–3658 (2007).
  • Molander GA , EllisN. Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.Acc. Chem. Res.40(4), 275–286 (2007).
  • Molander GA , FigueroaR. Organotrifluoroborates: expanding organoboron chemistry.Aldrichimica Acta38(2), 49–56 (2005).
  • Darses S , GenetJP. Potassium trifluoro(organo)borates: new perspectives in organic chemistry.Eur. J. Org. Chem. (22), 4313–4327 (2003).
  • Batey RA , QuachTD, ShenMet al. Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed C-C bond-forming reactions. Pure Appl. Chem. 74(1), 43–55 (2002).
  • Bunch JE , BumgardnerCL. Aryl trifluoromethyl acetylenes.J. Fluorine Chem.36(3), 313–317 (1987).
  • Molander GA , KatonaBW, MachrouhiF. Development of the Suzuki–Miyaura cross-coupling reaction: use of air-stable potassium alkynyltrifluoroborates in aryl alkynylations.J. Org. Chem.67(24), 8416–8423 (2002).
  • Uenishi J , Beau J-M, Armstrong RW, Kishi Y. Dramatic rate enhancement of Suzuki diene synthesis. Its application to palytoxin synthesis. J. Am. Chem. Soc.109(15), 4756 (1987).
  • Gillmann T , WeeberT. Silver oxide-assisted palladium-catalyzed cross coupling of methyl 2-halo-2,3-butadienoates with arylboronic acids.Synlett (8), 649–650 (1994).
  • Chen H , DengMZ. A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids. Org. Lett.2(12), 1649–1651 (2000).
  • Frohn HJ , AdoninNY, BardinVV, StarichenkoVF. Highly efficient cross-coupling reactions with the perfluoroorganotrifluoroborate salts K [RfBF3] (Rf =C6F5, CF2=CF). Tetrahedron Lett.43(45), 8111–8114 (2002).
  • Hirabayashi K , MoriA, KawashimaJet al. Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide. J. Org. Chem. 65(17), 5342–5349 (2000).
  • Fei Z , ZhaoD, GeldbachTJ, ScopellitiR, DysonPJ. Structure of nitrile-functionalized alkyltrifluoroborate salts.Eur. J. Inorg. Chem. (5), 860–865 (2005).
  • Shirakawa E , YoshidaH, KurahashiT, NakaoY, HiyamaT. Carbostannylation of alkynes catalyzed by an iminophosphine-palladium complex.J. Am. Chem. Soc.120(12), 2975–2976 (1998).
  • Shirakawa E , YoshidaH, NakaoY, HiyamaT. Palladium-catalyzed dimerization-carbostannylation of alkynes: synthesis of highly conjugated alkenylstannanes.J. Am. Chem. Soc.121(17), 4290–4291 (1999).
  • Shirakawa E , HiyamaT. The palladium-iminophosphine catalyst for the reactions of organostannanes.J. Organomet. Chem.576(1–2), 169–178 (1999).
  • Shirakawa E , YamasakiK, YoshidaH, HiyamaT. Nickel-catalyzed carbostannylation of alkynes with allyl-, acyl-, and alkynylstannanes: Stereoselective synthesis of trisubstituted vinylstannanes.J. Am. Chem. Soc.121(43), 10221–10222 (1999).
  • Shirakawa E , YoshidaH, NakaoY, HiyamaT. Mechanistic aspects of palladium-catalyzed allylstannylation of alkynes.Org. Lett.2(15), 2209–2211 (2000).
  • Shirakawa E , NakaoY, YoshidaH, HiyamaT. Nickel-catalyzed acylstannylation of 1,3-dienes: synthesis and reaction of α-oxoallylstannanes.J. Am. Chem. Soc.122(37), 9030–9031 (2000).
  • Shirakawa E , HiyamaT. Transition metal-catalyzed carbostannylation of alkynes and dienes.Bull. Chem. Soc. Jpn75(7), 1435–1450 (2002).
  • Shirakawa E , NakaoY, HiyamaT. Nickel-catalysed acylstannylation of 1,2-dienes: synthesis and reactions of α-(acylmethyl)vinylstannanes.Chem. Commun. (3), 263–264 (2001).
  • Shirakawa E , HiyamaT. Transition metal-catalyzed carbostannylation of alkynes and dienes.Bull. Chem. Soc. Jpn75(7), 1435–1450 (2002).
  • Shirakawa E , NakaoY, TsuchimotoT, HiyamaT. Synthesis of polycyclic compounds utilizing the nickel-catalysed alkynylstannylation of 1,2-dienes.Chem. Commun.8(17), 1962–1963 (2002).
  • Shirakawa E , HiyamaT. Synthesis of functionalized alkenes by transition metal-catalyzed carbostannylations of alkynes and dienes followed by cross-coupling reactions.J. Organomet. Chem.653(1–2), 114–121 (2002).
  • Shirakawa E , YamamotoY, NakaoYet al. Nickel-catalyzed tandem carbostannylation of alkynes and 1,2-dienes with alkynylstannanes. Angew. Chem. Int. Ed. 43(26), 3448–3451 (2004).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.