Nucleophilic 18 F‐Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors: Advantages and Disadvantages
The field of labeling electron‐rich aryl compounds with nucleophilic [ 18 F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically div...
Saved in:
| Published in | European journal of organic chemistry Vol. 2017; no. 3; pp. 453 - 458 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
18.01.2017
|
| Online Access | Get full text |
Cover
Loading…
| Abstract | The field of labeling electron‐rich aryl compounds with nucleophilic [
18
F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters. |
|---|---|
| AbstractList | The field of labeling electron‐rich aryl compounds with nucleophilic [
18
F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters. |
| Author | Kristensen, Jesper Langgaard Petersen, Ida Nymann Herth, Matthias Manfred |
| Author_xml | – sequence: 1 givenname: Ida Nymann surname: Petersen fullname: Petersen, Ida Nymann organization: University of Copenhagen Department of Drug Design and Pharmacology Jagtvej 160 2100 Copenhagen Denmark – sequence: 2 givenname: Jesper Langgaard orcidid: 0000-0002-5613-1267 surname: Kristensen fullname: Kristensen, Jesper Langgaard organization: University of Copenhagen Department of Drug Design and Pharmacology Jagtvej 160 2100 Copenhagen Denmark – sequence: 3 givenname: Matthias Manfred surname: Herth fullname: Herth, Matthias Manfred organization: University of Copenhagen Department of Drug Design and Pharmacology Jagtvej 160 2100 Copenhagen Denmark, Rigshospitalet Department of Clinical Physiology, Nuclear Medicine and PET Blegdamsvej 9 2100 Copenhagen Denmark |
| BookMark | eNo9kM1KQkEUx4cwSK1t63mBa_N5P9qZaQlSQi5qdRnPPddGrjMyo4HQokfoGXuSrhSu_l9w4Px6pOO8Q0KuORtwxsQNrj0MBOMp40rlZ6TLWVEkLC1Yp_VKqoQX8vWC9GJcM8aKNOVd8vm0hwb99t02FijP6eTn63tmlthYt6K-pi9bGzwc4DhPfeWd3W_oW2MrpD7QOx_aBujcOgO-oeO4w0DnAWEfog_xlg6rD-N2ZoWRGlfRexvNqbkk57VpIl79a58sJuPF6DGZPT9MR8NZArnKk0pKLXkmGRRMFJBXNQpudPtyhjwToIXmAKJOVaUw00rrjCMsQaI0bUDZJ4O_sxB8jAHrchvsxoRDyVl5RFce0ZUndPIX2jRl0g |
| CitedBy_id | crossref_primary_10_1002_ange_201805501 crossref_primary_10_1039_C7OB00628D crossref_primary_10_1021_acsptsci_1c00133 crossref_primary_10_1007_s40336_020_00368_y crossref_primary_10_1021_acs_jmedchem_9b01692 crossref_primary_10_1021_acs_joc_7b02467 crossref_primary_10_1039_C9OB01187K crossref_primary_10_1039_D1SC02789A crossref_primary_10_1002_tcr_202300072 crossref_primary_10_1016_j_ejmech_2020_112629 crossref_primary_10_1021_acs_oprd_9b00021 crossref_primary_10_1007_s10967_020_07475_0 crossref_primary_10_1002_jlcr_3570 crossref_primary_10_1002_chem_202104169 crossref_primary_10_1038_s41596_019_0149_3 crossref_primary_10_1002_ajoc_201800494 crossref_primary_10_1002_anie_201805501 crossref_primary_10_1002_cmdc_202200472 crossref_primary_10_1016_j_tetlet_2022_154010 crossref_primary_10_3390_molecules24193436 crossref_primary_10_1039_D2OB00133K |
| Cites_doi | 10.1021/jm400770g 10.1039/C6CC03295H 10.1039/C4RA00674G 10.1002/chem.201405586 10.1016/j.jfluchem.2010.04.004 10.1021/ol501243g 10.1021/jm400156p 10.3390/molecules20010470 10.3390/molecules16097621 10.1126/science.1212625 10.1038/ncomms5365 10.1021/ol052633u 10.1039/C39950002215 10.1021/acs.orglett.5b02875 10.1002/jlcr.1853 10.1002/anie.201505927 10.1002/anie.201404436 10.1002/ejoc.201600705 10.1021/ja066850h 10.2967/jnumed.114.151332 10.1039/C6SC00197A 10.1021/acs.joc.5b02332 10.1021/jo800727s 10.1021/ja409748m 10.1002/ange.201505927 10.1002/ange.201404436 10.1021/ja3084797 |
| ContentType | Journal Article |
| DBID | AAYXX CITATION |
| DOI | 10.1002/ejoc.201601448 |
| DatabaseName | CrossRef |
| DatabaseTitle | CrossRef |
| DatabaseTitleList | CrossRef |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1099-0690 |
| EndPage | 458 |
| ExternalDocumentID | 10_1002_ejoc_201601448 |
| GroupedDBID | -~X .3N .GA 05W 0R~ 10A 1L6 1OC 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AABCJ AAESR AAEVG AAHHS AAMNL AANLZ AAONW AASGY AAXRX AAYXX AAZKR ABCQN ABCUV ABDBF ABEML ABIJN ABJNI ABLJU ABPVW ACAHQ ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACSCC ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFZJQ AHBTC AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BY8 CITATION CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EJD F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2P P2W P2X P4D Q.N Q11 QB0 QRW R.K ROL RWI RX1 SUPJJ TN5 UB1 UPT V2E W8V W99 WBFHL WBKPD WH7 WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XV2 ~IA ~WT |
| ID | FETCH-LOGICAL-c848-d33531730c9029c8dfe21a50027e172c5251cc2f64d4e7545571ecbc3e3a455e3 |
| ISSN | 1434-193X |
| IngestDate | Fri Dec 06 01:10:54 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 3 |
| Language | English |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c848-d33531730c9029c8dfe21a50027e172c5251cc2f64d4e7545571ecbc3e3a455e3 |
| ORCID | 0000-0002-5613-1267 |
| PageCount | 6 |
| ParticipantIDs | crossref_primary_10_1002_ejoc_201601448 |
| PublicationCentury | 2000 |
| PublicationDate | 2017-01-18 |
| PublicationDateYYYYMMDD | 2017-01-18 |
| PublicationDate_xml | – month: 01 year: 2017 text: 2017-01-18 day: 18 |
| PublicationDecade | 2010 |
| PublicationTitle | European journal of organic chemistry |
| PublicationYear | 2017 |
| References | e_1_2_5_23_3 e_1_2_5_23_1 e_1_2_5_23_2 e_1_2_5_24_1 e_1_2_5_21_1 e_1_2_5_22_1 Ross T. L. (e_1_2_5_4_1) 2005; 48 e_1_2_5_20_1 e_1_2_5_15_1 e_1_2_5_13_2 e_1_2_5_14_1 e_1_2_5_17_1 e_1_2_5_9_1 e_1_2_5_15_2 e_1_2_5_16_1 e_1_2_5_8_1 e_1_2_5_11_1 e_1_2_5_7_1 e_1_2_5_10_1 e_1_2_5_4_3 e_1_2_5_6_1 e_1_2_5_13_1 e_1_2_5_4_2 e_1_2_5_5_1 e_1_2_5_11_2 e_1_2_5_12_1 e_1_2_5_3_1 e_1_2_5_2_1 e_1_2_5_19_1 e_1_2_5_17_2 e_1_2_5_18_1 |
| References_xml | – ident: e_1_2_5_8_1 doi: 10.1021/jm400770g – ident: e_1_2_5_20_1 doi: 10.1039/C6CC03295H – ident: e_1_2_5_10_1 doi: 10.1039/C4RA00674G – ident: e_1_2_5_16_1 doi: 10.1002/chem.201405586 – ident: e_1_2_5_6_1 doi: 10.1016/j.jfluchem.2010.04.004 – ident: e_1_2_5_7_1 doi: 10.1021/ol501243g – volume: 48 start-page: S153 year: 2005 ident: e_1_2_5_4_1 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Ross T. L. – ident: e_1_2_5_5_1 doi: 10.1021/jm400156p – ident: e_1_2_5_19_1 doi: 10.3390/molecules20010470 – ident: e_1_2_5_4_3 doi: 10.3390/molecules16097621 – ident: e_1_2_5_15_1 doi: 10.1126/science.1212625 – ident: e_1_2_5_11_1 doi: 10.1038/ncomms5365 – ident: e_1_2_5_23_3 doi: 10.1021/ol052633u – ident: e_1_2_5_2_1 doi: 10.1039/C39950002215 – ident: e_1_2_5_18_1 doi: 10.1021/acs.orglett.5b02875 – ident: e_1_2_5_22_1 – ident: e_1_2_5_3_1 doi: 10.1002/jlcr.1853 – ident: e_1_2_5_13_1 doi: 10.1002/anie.201505927 – ident: e_1_2_5_17_1 doi: 10.1002/anie.201404436 – ident: e_1_2_5_21_1 doi: 10.1002/ejoc.201600705 – ident: e_1_2_5_4_2 doi: 10.1021/ja066850h – ident: e_1_2_5_12_1 doi: 10.2967/jnumed.114.151332 – ident: e_1_2_5_11_2 doi: 10.1039/C6SC00197A – ident: e_1_2_5_14_1 doi: 10.1021/acs.joc.5b02332 – ident: e_1_2_5_23_1 doi: 10.1021/jo800727s – ident: e_1_2_5_9_1 – ident: e_1_2_5_23_2 doi: 10.1021/ja409748m – ident: e_1_2_5_24_1 – ident: e_1_2_5_13_2 doi: 10.1002/ange.201505927 – ident: e_1_2_5_17_2 doi: 10.1002/ange.201404436 – ident: e_1_2_5_15_2 doi: 10.1021/ja3084797 |
| SSID | ssj0009661 |
| Score | 2.2330673 |
| Snippet | The field of labeling electron‐rich aryl compounds with nucleophilic [
18
F]fluoride has recently expanded with radiofluorination strategies that apply boronic... |
| SourceID | crossref |
| SourceType | Aggregation Database |
| StartPage | 453 |
| Title | Nucleophilic 18 F‐Labeling of Spirocyclic Iodonium Ylide or Boronic Pinacol Ester Precursors: Advantages and Disadvantages |
| Volume | 2017 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LbtNAFB2FsoBNxVNAAc0CiYVliO3xix2URm1VskBBCqtofD2ujKgdpcmiiAWfwE_xI3wJ987DdqBIhY0VT2xHyT26987kzDmMPStBEnkw9Sv641DkMvclqMyXZZzJRKWhAtrv_G6aHH4Qx_N4Phr9GLCWNuviBXy5dF_J_0QVxzCutEv2HyLbPRQH8DXGF48YYTxeKcZTEiNul7QmAl6QeZOOunAiC7PRnPakLGusUhdAFx3hLLSpN2fex891SZ5O3pvWmuDUDSlYeweknEDMDNhgL77SjDltvbyWJAehmcv1uexG_rq0b9tcYxsFHjhnuT4Zk7CnyXpHpfSmF2ey6TkBlHxUY98_ViRo7p3I5vRUWh0As4JrCY7atryW50TnqZz7qF3MCIj16m_lXxEJH3vKuSlPZmyshRKMq6hL2nTzAJ7RIAcLoz5sy7kwyvB_VAqjPKs-taRjGSQ0scz6muh4AL-Vyo7AaMSewwXdv-juv8aukx4jWTi8fd-rmOGMUs_73Xdz2qHj8OX25w96o0GTM7vFdu3shL82ULvNRqq5w27su9DdZV-HkONBxic_v313YONtxQdg4w5sXIONtytuwcYt2LgGG-_B9or3UOMINb4FtXtsNjmY7R_61sDDh0xkfhlFmOGxhEA-DnPIykqFATlwhKnCvhli7K0BwioRpVAptvJxGigoIFKRxBMV3Wc7TduoB4xjk5vkSmLiKCW1_IUcQ5THgOcppGHwkD13v9xiaWRaFpfH6NGVr9xjN3uIPmY769VGPcEOdF081fH9BQniixA |
| link.rule.ids | 314,780,784,27924,27925 |
| linkProvider | Wiley-Blackwell |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Nucleophilic+18+F%E2%80%90Labeling+of+Spirocyclic+Iodonium+Ylide+or+Boronic+Pinacol+Ester+Precursors%3A+Advantages+and+Disadvantages&rft.jtitle=European+journal+of+organic+chemistry&rft.au=Petersen%2C+Ida+Nymann&rft.au=Kristensen%2C+Jesper+Langgaard&rft.au=Herth%2C+Matthias+Manfred&rft.date=2017-01-18&rft.issn=1434-193X&rft.eissn=1099-0690&rft.volume=2017&rft.issue=3&rft.spage=453&rft.epage=458&rft_id=info:doi/10.1002%2Fejoc.201601448&rft.externalDBID=n%2Fa&rft.externalDocID=10_1002_ejoc_201601448 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1434-193X&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1434-193X&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1434-193X&client=summon |