Deuterodehalogenation—a mild method for synthesising deuterated heterocycles
[Display omitted] We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D8-IPA or Et3SiD under palladium-catalysed conditions.
Saved in:
Published in | Tetrahedron letters Vol. 55; no. 22; pp. 3305 - 3307 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
28.05.2014
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | [Display omitted]
We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D8-IPA or Et3SiD under palladium-catalysed conditions. |
---|---|
AbstractList | [Display omitted]
We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D8-IPA or Et3SiD under palladium-catalysed conditions. We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D-8-IPA or Et3SiD under palladium-catalysed conditions. (C) 2014 Elsevier Ltd. All rights reserved. We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D sub(8)-IPA or Et sub(3)SiD under palladium-catalysed conditions. |
Author | Noonan, Gary M. Roberts, Bryan Durham, Emma C. Donald, Craig S. Moss, Thomas A. |
Author_xml | – sequence: 1 givenname: Craig S. surname: Donald fullname: Donald, Craig S. email: craig.donald@astrazeneca.com – sequence: 2 givenname: Thomas A. surname: Moss fullname: Moss, Thomas A. – sequence: 3 givenname: Gary M. surname: Noonan fullname: Noonan, Gary M. – sequence: 4 givenname: Bryan surname: Roberts fullname: Roberts, Bryan – sequence: 5 givenname: Emma C. surname: Durham fullname: Durham, Emma C. |
BookMark | eNqNkM9qGzEQh0VIILbTN8hhj4Gy7mgle6VLoLjpHzDtJT2LXWnWlllLjiQn-NaHyBP2SSJ7TY-hw8CA9PuG4RuTS-cdEnJLYUqBzj9tpglTj2laAeVTyF3NLsiIipqVbCboJRkBcCg5MHlNxjFuINdcwIj8_IL7hMEbXDe9X6FrkvXu75_Xptja3hRbTGtvis6HIh5cWmO00bpVYU5Yk9AUazwu0AfdY7whV13TR_xwnhPy--vD4-J7ufz17cfi87LUjMlUNkLOBJOd5KIFbTrdtrRjAjgaoFIbpKzKz_kThOC1ZLURVVVzyeetkFixCbkb9u6Cf9pjTGpro8a-bxz6fVS05nwuqRQ0R_kQ1cHHGLBTu2C3TTgoCuqoT23UoE8d9SnIXc0y9nHAXrD1XdQWncZ_aNbHWF2BrI8meU6L_08vbDpZXvi9Sxm9H1DMvp4tBnXGjQ2okzLevn_pG1rMn28 |
CitedBy_id | crossref_primary_10_3390_molecules28062869 crossref_primary_10_1021_acs_joc_6b01609 crossref_primary_10_1021_acs_orglett_0c00001 crossref_primary_10_1039_D4CC00474D crossref_primary_10_1002_chin_201445063 crossref_primary_10_1016_S1872_2067_23_64624_8 crossref_primary_10_1021_jacs_8b07597 crossref_primary_10_1002_chem_202100635 crossref_primary_10_1021_acs_orglett_3c03281 crossref_primary_10_1016_j_tet_2019_02_054 crossref_primary_10_1002_adsc_201601105 crossref_primary_10_1016_j_tetlet_2017_05_092 crossref_primary_10_1021_acs_joc_1c00573 crossref_primary_10_1002_anie_202218858 crossref_primary_10_1039_D0GC01649G crossref_primary_10_1002_ange_202218858 crossref_primary_10_1016_j_tetlet_2024_155152 crossref_primary_10_1021_acsnano_9b05523 |
Cites_doi | 10.1055/s-2004-831337 10.1002/jlcr.1905 10.1080/10256016.2010.488808 10.1080/00268970500038451 10.1358/dnp.2010.23.6.1426638 10.1124/dmd.111.042770 10.1021/jo048715y 10.1021/om400713y 10.1021/ol061738+ 10.1016/j.tetlet.2013.06.063 10.1002/jlcr.3090 10.1021/ja029853c 10.1021/ja01111a024 10.1002/jlcr.2580230809 10.1002/(SICI)1099-1344(199701)39:1<49::AID-JLCR938>3.0.CO;2-M 10.1021/jm1010995 10.1002/(SICI)1099-1344(199912)42:12<1125::AID-JLCR266>3.0.CO;2-9 |
ContentType | Journal Article |
Copyright | 2014 Elsevier Ltd |
Copyright_xml | – notice: 2014 Elsevier Ltd |
DBID | 1KM 1KN BLEPL DTL GNMZZ AAYXX CITATION 7SR 7U5 8BQ 8FD JG9 L7M |
DOI | 10.1016/j.tetlet.2014.04.025 |
DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2014 CrossRef Engineered Materials Abstracts Solid State and Superconductivity Abstracts METADEX Technology Research Database Materials Research Database Advanced Technologies Database with Aerospace |
DatabaseTitle | Web of Science CrossRef Materials Research Database Engineered Materials Abstracts Solid State and Superconductivity Abstracts Technology Research Database Advanced Technologies Database with Aerospace METADEX |
DatabaseTitleList | Web of Science Materials Research Database |
Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1873-3581 |
EndPage | 3307 |
ExternalDocumentID | 10_1016_j_tetlet_2014_04_025 000337209700004 S0040403914006248 |
GroupedDBID | --- --K --M -ET -~X .~1 0R~ 123 1B1 1RT 1~. 1~5 4.4 457 4G. 53G 5VS 7-5 71M 85S 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKJ AAKOC AALRI AAOAW AAQFI AARLI AATCM AAXUO ABFNM ABFRF ABGSF ABJNI ABMAC ABPPZ ABUDA ABXDB ABYKQ ABZDS ACBEA ACDAQ ACGFS ACNCT ACRLP ADBBV ADECG ADEZE ADUVX AEBSH AEFWE AEHWI AEKER AENEX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q GBLVA IH2 J1W K-O KOM M2Z M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 RIG RNS ROL RPZ SCC SDF SDG SDP SES SPC SPCBC SSK SSP SSU SSZ T5K TN5 TWZ WH7 XPP XSW YK3 YR2 ZMT ~02 ~G- ~KM 1KM 1KN AAHBH AAXKI AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED .GJ .HR 186 29Q 3EH 6TJ AAQXK AAYOK AAYXX ACBNA ACKIV ACNNM ADMUD ADVLN AFFNX AFJKZ AGRDE ASPBG AVWKF AZFZN CITATION D0S FEDTE FGOYB G8K HMS HVGLF HZ~ IHE MVM OHT R2- SCB SEW SOC UQL WUQ XJT Y6R YQJ ZCG ZKB ZXP 7SR 7U5 8BQ 8FD JG9 L7M |
ID | FETCH-LOGICAL-c339t-a895839f948b0cdfcbb1f3804ed019cde132cdf8b008847937d82274946b89e23 |
IEDL.DBID | .~1 |
ISICitedReferencesCount | 19 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000337209700004 |
ISSN | 0040-4039 |
IngestDate | Fri Oct 25 01:59:57 EDT 2024 Thu Sep 26 18:54:06 EDT 2024 Fri Nov 08 20:15:58 EST 2024 Wed Sep 18 07:17:39 EDT 2024 Fri Feb 23 02:19:34 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 22 |
Keywords | Deuterium Heterocycles UUFVKYYLLBDURI-UICOGKGYSA-N SRWDQSRTOOMPMO-UHFFFAOYSA-N FCEHBMOGCRZNNI-UICOGKGYSA-N AATZYZANFOSJCU-UHFFFAOYSA-N ISUZVEMVSHSJED-UHFFFAOYSA-N YMTINGFKWWXKFG-UHFFFAOYSA-N Deuterodehalogenation GDLIGKIOYRNHDA-UHFFFAOYSA-N AHOIGFLSEXUWNV-UICOGKGYSA-N UKCBGXCNXOKVTF-UHFFFAOYSA-N RJXLUGSJEMSDPK-BNEYPBHNSA-N SMWDFEZZVXVKRB-WFVSFCRTSA-N OWPIFQXNMLDXKW-QYKNYGDISA-N PBWDRTGTQIXVBR-UHFFFAOYSA-N PVLIRTAXXPPHCJ-UHFFFAOYSA-N Metabolism VVJLDCRGRQKTCJ-UHFFFAOYSA-N BCGWQEUPMDMJNV-UICOGKGYSA-N CKJWDLCHHHACAN-QOWOAITPSA-N YEEDHQBGXCVRDP-QYKNYGDISA-N ZZOWFLAMMWOSCG-UHFFFAOYSA-N RWYLZMUAGRBIDC-UICOGKGYSA-N KUIUUMNWANUECJ-QYKNYGDISA-N ZGIKWINFUGEQEO-UHFFFAOYSA-N FVUFTABOJFRHSU-UHFFFAOYSA-N MNEIJGDSFRHGMS-WORMITQPSA-N INDOLE DRUGS |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c339t-a895839f948b0cdfcbb1f3804ed019cde132cdf8b008847937d82274946b89e23 |
Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
PQID | 1744691981 |
PQPubID | 23500 |
PageCount | 3 |
ParticipantIDs | crossref_primary_10_1016_j_tetlet_2014_04_025 webofscience_primary_000337209700004 elsevier_sciencedirect_doi_10_1016_j_tetlet_2014_04_025 proquest_miscellaneous_1744691981 webofscience_primary_000337209700004CitationCount |
PublicationCentury | 2000 |
PublicationDate | 2014-05-28 |
PublicationDateYYYYMMDD | 2014-05-28 |
PublicationDate_xml | – month: 05 year: 2014 text: 2014-05-28 day: 28 |
PublicationDecade | 2010 |
PublicationPlace | OXFORD |
PublicationPlace_xml | – name: OXFORD |
PublicationTitle | Tetrahedron letters |
PublicationTitleAbbrev | TETRAHEDRON LETT |
PublicationYear | 2014 |
Publisher | Elsevier Ltd Elsevier |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
References | Bei, Hagemeyer, Volpe, Saxton, Turner, Guram (b0085) 2004; 69 Lauer, Noland (b0060) 1953; 75 Ghini, Burton, Gros (b0050) 1986; 23 Boyle, Mague, Fink (b0080) 2003; 125 Kerekes, Esposite, Doll, Tagat, Yu, Xiao, Zhang, Prelusky, Tevar, Gray, Terracina, Lee, Jones, Liu, Basso, Smith (b0005) 2011; 54 Noonan, Hayter, Campbell, Gorman, Partridge, Lamont (b0070) 2013; 54 Sharma, Strelevitz, Gao, Clark, Schildknegt, Obach, Ripp, Spracklin, Tremaine, Vaz (b0015) 2012; 40 Huber, Grassi, Bauder (b0035) 2005; 103 Czeskis (b0045) 1997; 39 Schofield, Brasseur, Bruin, Vassal, Klieber, Arabeyre, Bourrie, Sadoun, Fabre (b0010) 2013; 56 Morgan, Nguyen, Uttamsingh, Bridson, Harbeson, Tung, Masse (b0025) 2011; 54 Molina de la Torre, Espinet, Albeniz (b0075) 2013; 32 Dietrich, Fels (b0040) 1999; 42 Winnicka, Dabrowski, Winek, Kanska (b0030) 2010; 46 Shao, Hewitt (b0020) 2010; 23 Koketsu, Oguri, Watanabe, Oikawa (b0055) 2006; 8 Pierrat, Gros, Fort (b0065) 2004 Huber, S (WOS:000229182200006) 2005; 103 Boyle, RC (WOS:000181555600019) 2003; 125 Noonan, GM (WOS:000322608000005) 2013; 54 LAUER, WM (WOS:A1953UB52800024) 1953; 75 Shao, LM (WOS:000282038900007) 2010; 23 Bei, XH (WOS:000225550300008) 2004; 69 Kerekes, AD (WOS:000285818000015) 2011; 54 Pierrat, P (WOS:000225092300013) 2004 Dietrich, A (WOS:000083929300001) 1999; 42 Sharma, R (WOS:000300610100027) 2012; 40 Schofield, J (WOS:000325088900019) 2013; 56 de la Torre, JAM (WOS:000326122600028) 2013; 32 Czeskis, BA (WOS:A1997WF38900006) 1997; 39 Koketsu, K (WOS:000241030900013) 2006; 8 GHINI, AA (WOS:A1986D846600008) 1986; 23 Morgan, AJ (WOS:000295901500006) 2011; 54 Winnicka, E (WOS:000279219100009) 2010; 46 Ghini (10.1016/j.tetlet.2014.04.025_b0050) 1986; 23 Czeskis (10.1016/j.tetlet.2014.04.025_b0045) 1997; 39 Morgan (10.1016/j.tetlet.2014.04.025_b0025) 2011; 54 Shao (10.1016/j.tetlet.2014.04.025_b0020) 2010; 23 Bei (10.1016/j.tetlet.2014.04.025_b0085) 2004; 69 Kerekes (10.1016/j.tetlet.2014.04.025_b0005) 2011; 54 Noonan (10.1016/j.tetlet.2014.04.025_b0070) 2013; 54 Molina de la Torre (10.1016/j.tetlet.2014.04.025_b0075) 2013; 32 Dietrich (10.1016/j.tetlet.2014.04.025_b0040) 1999; 42 Pierrat (10.1016/j.tetlet.2014.04.025_b0065) 2004 Boyle (10.1016/j.tetlet.2014.04.025_b0080) 2003; 125 Koketsu (10.1016/j.tetlet.2014.04.025_b0055) 2006; 8 Huber (10.1016/j.tetlet.2014.04.025_b0035) 2005; 103 Schofield (10.1016/j.tetlet.2014.04.025_b0010) 2013; 56 Lauer (10.1016/j.tetlet.2014.04.025_b0060) 1953; 75 Sharma (10.1016/j.tetlet.2014.04.025_b0015) 2012; 40 Winnicka (10.1016/j.tetlet.2014.04.025_b0030) 2010; 46 |
References_xml | – volume: 103 start-page: 1395 year: 2005 end-page: 1409 ident: b0035 publication-title: Mol. Phys. contributor: fullname: Bauder – volume: 39 start-page: 49 year: 1997 ident: b0045 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Czeskis – volume: 46 start-page: 225 year: 2010 end-page: 232 ident: b0030 publication-title: Isot. Environ. Health Stud. contributor: fullname: Kanska – volume: 8 start-page: 4719 year: 2006 end-page: 4722 ident: b0055 publication-title: Org. Lett. contributor: fullname: Oikawa – volume: 54 start-page: 613 year: 2011 end-page: 624 ident: b0025 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Masse – volume: 42 start-page: 1125 year: 1999 ident: b0040 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Fels – start-page: 2319 year: 2004 end-page: 2322 ident: b0065 publication-title: Synlett contributor: fullname: Fort – volume: 56 start-page: 504 year: 2013 end-page: 512 ident: b0010 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Fabre – volume: 125 start-page: 3228 year: 2003 end-page: 3229 ident: b0080 publication-title: J. Am. Chem. Soc. contributor: fullname: Fink – volume: 54 start-page: 201 year: 2011 end-page: 210 ident: b0005 publication-title: J. Med. Chem. contributor: fullname: Smith – volume: 69 start-page: 8626 year: 2004 end-page: 8633 ident: b0085 publication-title: J. Org. Chem. contributor: fullname: Guram – volume: 23 start-page: 857 year: 1986 end-page: 859 ident: b0050 publication-title: J. Labelled Compd. Radiopharm. contributor: fullname: Gros – volume: 54 start-page: 4518 year: 2013 end-page: 4521 ident: b0070 publication-title: Tetrahedron Lett. contributor: fullname: Lamont – volume: 40 start-page: 625 year: 2012 end-page: 634 ident: b0015 publication-title: Drug Metab. Dispos. contributor: fullname: Vaz – volume: 23 start-page: 398 year: 2010 end-page: 404 ident: b0020 publication-title: Drug News Perspect. contributor: fullname: Hewitt – volume: 32 start-page: 5428 year: 2013 end-page: 5434 ident: b0075 publication-title: Organometallics contributor: fullname: Albeniz – volume: 75 start-page: 3689 year: 1953 end-page: 3692 ident: b0060 publication-title: J. Am. Chem. Soc. contributor: fullname: Noland – start-page: 2319 year: 2004 ident: WOS:000225092300013 article-title: Unusual t-BuLi induced ortholithiation versus halogen-lithium exchange in bromopyridines: Two alternative strategies for functionalization publication-title: SYNLETT doi: 10.1055/s-2004-831337 contributor: fullname: Pierrat, P – volume: 39 start-page: 49 year: 1997 ident: WOS:A1997WF38900006 article-title: Synthesis of multidrug resistance modulator LY335979 labeled with deuterium and tritium publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS contributor: fullname: Czeskis, BA – volume: 54 start-page: 613 year: 2011 ident: WOS:000295901500006 article-title: Design and synthesis of deuterated boceprevir analogs with enhanced pharmacokinetic properties publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS doi: 10.1002/jlcr.1905 contributor: fullname: Morgan, AJ – volume: 46 start-page: 225 year: 2010 ident: WOS:000279219100009 article-title: The kinetic and solvent deuterium isotope effects in the 4-and 5-positions of the indole ring on the enzymatic decomposition of L-tryptophan publication-title: ISOTOPES IN ENVIRONMENTAL AND HEALTH STUDIES doi: 10.1080/10256016.2010.488808 contributor: fullname: Winnicka, E – volume: 103 start-page: 1395 year: 2005 ident: WOS:000229182200006 article-title: Structure and symmetry of azulene as determined from microwave spectra of isotopomers publication-title: MOLECULAR PHYSICS doi: 10.1080/00268970500038451 contributor: fullname: Huber, S – volume: 23 start-page: 398 year: 2010 ident: WOS:000282038900007 article-title: THE KINETIC ISOTOPE EFFECT IN THE SEARCH FOR DEUTERATED DRUGS publication-title: DRUG NEWS & PERSPECTIVES doi: 10.1358/dnp.2010.23.6.1426638 contributor: fullname: Shao, LM – volume: 40 start-page: 625 year: 2012 ident: WOS:000300610100027 article-title: Deuterium Isotope Effects on Drug Pharmacokinetics. I. System-Dependent Effects of Specific Deuteration with Aldehyde Oxidase Cleared Drugs publication-title: DRUG METABOLISM AND DISPOSITION doi: 10.1124/dmd.111.042770 contributor: fullname: Sharma, R – volume: 69 start-page: 8626 year: 2004 ident: WOS:000225550300008 article-title: Productive chloroarene C-Cl bond activation: Palladium/phosphine-catalyzed methods for oxidation of alcohols and hydrodechlorination of chloroarenes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo048715y contributor: fullname: Bei, XH – volume: 32 start-page: 5428 year: 2013 ident: WOS:000326122600028 article-title: Solvent-Induced Reduction of Palladium-Aryls, a Potential Interference in Pd Catalysis publication-title: ORGANOMETALLICS doi: 10.1021/om400713y contributor: fullname: de la Torre, JAM – volume: 54 start-page: 201 year: 2011 ident: WOS:000285818000015 article-title: Aurora Kinase Inhibitors Based on the Imidazo[1,2-a]pyrazine Core Fluorine and Deuterium Incorporation Improve Oral Absorption and Exposure publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Kerekes, AD – volume: 75 start-page: 3689 year: 1953 ident: WOS:A1953UB52800024 article-title: THE NITRATION OF MONODEUTEROBENZE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LAUER, WM – volume: 42 start-page: 1125 year: 1999 ident: WOS:000083929300001 article-title: Synthesis of H-3-tolperisone publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS contributor: fullname: Dietrich, A – volume: 8 start-page: 4719 year: 2006 ident: WOS:000241030900013 article-title: Identification and stereochemical assignment of the beta-hydroxytryptophan intermediate in the echinomycin biosynthetic pathway publication-title: ORGANIC LETTERS doi: 10.1021/ol061738+ contributor: fullname: Koketsu, K – volume: 54 start-page: 4518 year: 2013 ident: WOS:000322608000005 article-title: Expanding the scope of silane-mediated hydrodehalogenation reactions publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2013.06.063 contributor: fullname: Noonan, GM – volume: 23 start-page: 857 year: 1986 ident: WOS:A1986D846600008 article-title: SYNTHESES OF (6-H-2) INDOLE, (6-H-2) GRAMINE AND (6-H-3) GRAMINE publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS contributor: fullname: GHINI, AA – volume: 56 start-page: 504 year: 2013 ident: WOS:000325088900019 article-title: Effect of deuteration on the metabolism and clearance of some pharmacologically active compounds-synthesis and in vitro metabolism of deuterated derivatives of dronedadrone publication-title: JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS doi: 10.1002/jlcr.3090 contributor: fullname: Schofield, J – volume: 125 start-page: 3228 year: 2003 ident: WOS:000181555600019 article-title: The first stable mononuclear silyl palladium hydrides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja029853c contributor: fullname: Boyle, RC – volume: 23 start-page: 398 year: 2010 ident: 10.1016/j.tetlet.2014.04.025_b0020 publication-title: Drug News Perspect. doi: 10.1358/dnp.2010.23.6.1426638 contributor: fullname: Shao – volume: 46 start-page: 225 year: 2010 ident: 10.1016/j.tetlet.2014.04.025_b0030 publication-title: Isot. Environ. Health Stud. doi: 10.1080/10256016.2010.488808 contributor: fullname: Winnicka – volume: 75 start-page: 3689 year: 1953 ident: 10.1016/j.tetlet.2014.04.025_b0060 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01111a024 contributor: fullname: Lauer – volume: 32 start-page: 5428 year: 2013 ident: 10.1016/j.tetlet.2014.04.025_b0075 publication-title: Organometallics doi: 10.1021/om400713y contributor: fullname: Molina de la Torre – volume: 8 start-page: 4719 year: 2006 ident: 10.1016/j.tetlet.2014.04.025_b0055 publication-title: Org. Lett. doi: 10.1021/ol061738+ contributor: fullname: Koketsu – volume: 23 start-page: 857 year: 1986 ident: 10.1016/j.tetlet.2014.04.025_b0050 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/jlcr.2580230809 contributor: fullname: Ghini – volume: 125 start-page: 3228 year: 2003 ident: 10.1016/j.tetlet.2014.04.025_b0080 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja029853c contributor: fullname: Boyle – volume: 40 start-page: 625 year: 2012 ident: 10.1016/j.tetlet.2014.04.025_b0015 publication-title: Drug Metab. Dispos. doi: 10.1124/dmd.111.042770 contributor: fullname: Sharma – volume: 103 start-page: 1395 year: 2005 ident: 10.1016/j.tetlet.2014.04.025_b0035 publication-title: Mol. Phys. doi: 10.1080/00268970500038451 contributor: fullname: Huber – volume: 54 start-page: 4518 year: 2013 ident: 10.1016/j.tetlet.2014.04.025_b0070 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2013.06.063 contributor: fullname: Noonan – volume: 56 start-page: 504 year: 2013 ident: 10.1016/j.tetlet.2014.04.025_b0010 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/jlcr.3090 contributor: fullname: Schofield – volume: 39 start-page: 49 year: 1997 ident: 10.1016/j.tetlet.2014.04.025_b0045 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/(SICI)1099-1344(199701)39:1<49::AID-JLCR938>3.0.CO;2-M contributor: fullname: Czeskis – start-page: 2319 year: 2004 ident: 10.1016/j.tetlet.2014.04.025_b0065 publication-title: Synlett contributor: fullname: Pierrat – volume: 54 start-page: 201 year: 2011 ident: 10.1016/j.tetlet.2014.04.025_b0005 publication-title: J. Med. Chem. doi: 10.1021/jm1010995 contributor: fullname: Kerekes – volume: 54 start-page: 613 year: 2011 ident: 10.1016/j.tetlet.2014.04.025_b0025 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/jlcr.1905 contributor: fullname: Morgan – volume: 42 start-page: 1125 year: 1999 ident: 10.1016/j.tetlet.2014.04.025_b0040 publication-title: J. Labelled Compd. Radiopharm. doi: 10.1002/(SICI)1099-1344(199912)42:12<1125::AID-JLCR266>3.0.CO;2-9 contributor: fullname: Dietrich – volume: 69 start-page: 8626 year: 2004 ident: 10.1016/j.tetlet.2014.04.025_b0085 publication-title: J. Org. Chem. doi: 10.1021/jo048715y contributor: fullname: Bei |
SSID | ssj0000680 |
Score | 2.2630062 |
Snippet | [Display omitted]
We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues... We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a... |
Source | Web of Science |
SourceID | proquest crossref webofscience elsevier |
SourceType | Aggregation Database Enrichment Source Index Database Publisher |
StartPage | 3305 |
SubjectTerms | Chemistry Chemistry, Organic Deuteration Deuterium Deuterodehalogenation Halides Heterocycles Metabolism Physical Sciences Science & Technology Tetrahedrons |
Title | Deuterodehalogenation—a mild method for synthesising deuterated heterocycles |
URI | https://dx.doi.org/10.1016/j.tetlet.2014.04.025 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000337209700004 https://search.proquest.com/docview/1744691981 |
Volume | 55 |
WOS | 000337209700004 |
WOSCitedRecordID | wos000337209700004 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8NAEB5KPehFfGJ9EaHX2Dy2ye5RqlIVe7LQ25J9lFY0KTY9eBF_hL_QX-JMHlKhoEhyyWY3LDPL7DeTb3YA2qLLA6OE5xpiuDJPK1cJHrmRjWJEz6FnfEpOvh9E_SG7HXVHDejVuTBEq6xsf2nTC2tdtXQqaXZm0ynl-DK8QoEughcFjBJ-GW5_uKbP3_wla8y9mjlHvev0uYLjlVtUCDEqfVYceEoFs1dvT0vwc8UGVWxG11uwWaFI56Kc6DY0bLoD6726eNsuDC4t1WrIjJ1QdMaWMb_P94_EeZ4-GacsHO0gYnXmrymCwPmUggaOKYYh_jTOhIgymX4l2tweDK-vHnp9tyqd4OowFLmbcFRCKMaCceVpM9ZK-eOQe8waxHTaWHRCsRlfopWh4FpsECnETLBIcWGDcB-aaZbaA3BUjPryUX8JeoKaKaXjMX5La8b9MNGiBW4tMTkrT8iQNXXsUZYSliRh6eEddFsQ12KVPzQt0Yj_MvKs1oJEcdKfjSS12WIu0a1CNx8n6begvaye7xmR70cFeURceEUt8P_SrVedk07nA-SH_574EWzQE5EOAn4MzfxlYU8Qy-TqtFisp7B2cXPXH3wBEC70ig |
link.rule.ids | 315,783,787,4509,24128,27936,27937,45597,45691 |
linkProvider | Elsevier |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8NAEB5qPdSL-MT6jNBraB7bZPdYqlJfPVnobck-SiuaFhsP3vwR_kJ_iTN5SIWCIskpmw3DTDL7zeabGYCW6PDAKOG5hhiuzNPKVYJHbmSjGNFz6BmfkpPvB1F_yG5GnVENelUuDNEqS99f-PTcW5dX2qU22_PplHJ8GR6hwBDBiwLG12Ad0YDAr3O9e33bHyw5ZO5V5DmaUGXQ5TSvzKJNiFTps7zmKfXMXr1CLSHQFWtUvh5dbcFmCSSdbiHrNtRsugONXtW_bRcGF5baNcyMndAGjS22_T7fPxLnefpknKJ3tIOg1Vm8pYgDF1PaN3BMPg0hqHEmxJWZ6Tdizu3B8Oryodd3y-4Jrg5DkbkJRzuEYiwYV542Y62UPw65x6xBWKeNxTgUL-MgOhraX4sNgoWYCRYpLmwQ7kM9naX2ABwVo8l8NGGCwaBmSul4jM_SmnE_TLRogltpTM6LIhmyYo89ykLDkjQsPTyDThPiSq3yh7El-vFfZp5XVpCoTvq5kaR29rqQGFlhpI9C-k1oLZvnWyIK_6gnj4jzwKgJ_l9u65Wl0qlEQHb4b8HPoNF_uL-Td9eD2yPYoBHiIAT8GOrZy6s9QWiTqdPy1f0CdW_3Pg |
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=Deuterodehalogenation-a+mild+method+for+synthesising+deuterated+heterocycles&rft.jtitle=Tetrahedron+letters&rft.au=Donald%2C+Craig+S.&rft.au=Moss%2C+Thomas+A.&rft.au=Noonan%2C+Gary+M.&rft.au=Roberts%2C+Bryan&rft.date=2014-05-28&rft.pub=Elsevier&rft.issn=0040-4039&rft.volume=55&rft.issue=22&rft.spage=3305&rft.epage=3307&rft_id=info:doi/10.1016%2Fj.tetlet.2014.04.025&rft.externalDBID=n%2Fa&rft.externalDocID=000337209700004 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon |