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6-Phosphorylated Phenanthridines From 2-isocyanobiphenyls Via Radical C-P And C-C Bond Formation.

Bo Zhang, C. Daniliuc, A. Studer
Published 2014 · Chemistry, Medicine

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A C-P bond and a C-C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitrile functionality and subsequent homolytic aromatic substitution. Various 6-phosphorylated phenanthridines are formed in moderate to excellent yield. In contrast to the currently intensively investigated direct arene phosphorylation, the arene core is constructed with concomitant phosphorylation using this approach.
This paper references
10.1021/OL0346640
Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides.
D. Gelman (2003)
Phosphorus : chemistry, biochemistry and technology
D. Corbridge (2012)
10.1021/CR9400626
Tandem Radical Reactions of Carbon Monoxide, Isonitriles, and Other Reagent Equivalents of the Geminal Radical Acceptor/Radical Precursor Synthon.
Ilhyong Ryu (1996)
10.1021/jo200299d
Photoinduced intramolecular cyclization of o-ethenylaryl isocyanides with organic disulfides mediated by diphenyl ditelluride.
T. Mitamura (2011)
A Guide to Organophosphorus Chemistry
L. D. Quin (2000)
10.1021/ol201222n
Palladium-catalyzed cross-coupling of H-phosphinate esters with chloroarenes.
E. Deal (2011)
10.1021/ol801935r
Microwave-assisted palladium-catalyzed cross-coupling of aryl and vinyl halides with H-phosphonate diesters.
M. Kalek (2008)
10.1039/b716519f
Phenanthridine synthesis via [2+2+2] cyclotrimerization reactions.
Lakshminath Sripada (2008)
10.1016/J.TET.2003.09.066
Chiral P,N-ligands with pyridine-nitrogen and phosphorus donor atoms. Syntheses and applications in asymmetric catalysis: Tetrahedron report number 659
G. Chelucci (2003)
10.1021/JO049657J
Hydrophosphorylation of alkenes with dialkyl phosphites catalyzed by Mn(III) under air.
O. Tayama (2004)
10.1021/OL052406S
Phosphonation of arenes with dialkyl phosphites catalyzed by Mn(II)/Co(II)/O2 redox couple.
Takashi Kagayama (2006)
10.1021/ol201141m
Ni(II)/Zn catalyzed reductive coupling of aryl halides with diphenylphosphine oxide in water.
X. Zhang (2011)
10.1039/c1cc12343b
Manganese(III)-mediated phosphinoyl radical reactions for stereoselective synthesis of phosphinoylated tetrahydronaphthalenes.
Xiangqiang Pan (2011)
10.1002/anie.201307211
An approach to benzophosphole oxides through silver- or manganese-mediated dehydrogenative annulation involving C-C and C-P bond formation.
Yuto Unoh (2013)
10.1002/chem.201103723
[NiCl2(dppp)]-catalyzed cross-coupling of aryl halides with dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphine.
Yu-Long Zhao (2012)
10.1021/jo301108g
Coupling reactions of heteroarenes with phosphites under silver catalysis.
Chang-Bing Xiang (2012)
10.1021/ja105070k
Memory of axial chirality in aryl radical phosphanylations.
Achim Bruch (2010)
10.1002/EJOC.201300545
Silver-Catalyzed Highly Regioselective Phosphonation of Arenes Bearing Electron-Withdrawing Groups
X. Mao (2013)
10.1021/ol200465z
Copper-catalyzed C-P bond construction via direct coupling of phenylboronic acids with H-phosphonate diesters.
Rongqiang Zhuang (2011)
10.1002/JHET.5570180202
A review of the chemistry of the antitumor benzo[c]phenanthridine alkaloids nitidine and fagaronine and of the related antitumor alkaloid coralyne
S. Phillips (1981)
10.1007/978-3-642-12073-2_4
Recent Advances in Metal-Catalyzed C–P Bond Formation
David S Glueck (2010)
10.1039/c2cc30429e
Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites.
Chaodong Hou (2012)
10.1021/OL051871M
Synthesis of a diverse series of phosphacoumarins with biological activity.
Xueshu Li (2005)
10.1002/anie.201306082
6-Trifluoromethyl-phenanthridines through radical trifluoromethylation of isonitriles.
Bo Zhang (2013)
10.1021/ol403147v
6-Aroylated phenanthridines via base promoted homolytic aromatic substitution (BHAS).
D. Leifert (2013)
10.1039/B618686F
Intermediate temperature proton conductors for PEM fuel cells based on phosphonic acid as protogenic group: a progress report.
H. Steininger (2007)
10.1021/ar400071v
Phosphinate chemistry in the 21st century: a viable alternative to the use of phosphorus trichloride in organophosphorus synthesis.
Jean-Luc Montchamp (2014)
10.1002/chem.200901473
Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
M. Andaloussi (2009)
10.1021/JA00243A050
Palladium-catalyzed substitutions of triflates derived from tyrosine-containing peptides and simpler hydroxyarenes forming 4-(diethoxyphosphinyl)phenylalanines and diethyl arylphosphonates
K. S. Petrakis (1987)
10.1021/ja404526x
Pd(II)-catalyzed phosphorylation of aryl C-H bonds.
Chen-Guo Feng (2013)
10.1021/OL0604421
Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines.
Birgit Janza (2006)
10.1002/ANIE.199526831
Cascade Radical Reactions of Isonitriles: A Second‐Generation Synthesis of (20S)‐Camptothecin, Topotecan, Irinotecan, and GI‐147211C
D. Curran (1996)
10.1021/ja408031s
Silver-catalyzed radical phosphonofluorination of unactivated alkenes.
Chengwei Zhang (2013)
10.1039/c0ob00243g
Arenediazonium tetrafluoroborates in palladium-catalyzed C-P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines.
Roberta Berrino (2010)
10.1039/C3GC00030C
Palladacycle-catalyzed phosphonation of aryl halides in neat water
Kai Xu (2013)
10.1039/B307538A
Palladium catalyzed cross-coupling reactions for phosphorus-carbon bond formation.
A. Schwan (2004)
10.1021/ol4000857
Cross dehydrogenative coupling via base-promoted homolytic aromatic substitution (BHAS): synthesis of fluorenones and xanthones.
Sebastian Wertz (2013)
10.1055/S-1981-29335
A Novel Synthesis of Dialkyl Arenephosphonates
T. Hirao (1981)
10.1002/ANIE.200701650
Homolytic substitution at phosphorus for the synthesis of alkyl and aryl phosphanes.
Santiago E Vaillard (2007)
10.1002/anie.201104114
Bis(phosphoryl)-bridged biphenyls by radical phosphanylation: synthesis and photophysical and electrochemical properties.
Achim Bruch (2011)
10.1039/b925951a
Manganese(III)-mediated direct phosphonation of arylalkenes and arylalkynes.
Xiangqiang Pan (2010)
10.1021/jo201030j
Palladium-catalyzed synthesis of dibenzophosphole oxides via intramolecular dehydrogenative cyclization.
Y. Kuninobu (2011)
10.1021/CR950026M
Manganese(III)-Based Oxidative Free-Radical Cyclizations.
B. Snider (1996)
10.1021/ol4022589
PhI(OAc)2-mediated synthesis of 6-(trifluoromethyl)phenanthridines by oxidative cyclization of 2-isocyanobiphenyls with CF3SiMe3 under metal-free conditions.
Qile Wang (2013)
10.1021/cr800315j
Direct phosphonylation of aromatic azaheterocycles.
Sarah Van der Jeught (2009)
10.1002/anie.201206115
Modular synthesis of phenanthridine derivatives by oxidative cyclization of 2-isocyanobiphenyls with organoboron reagents.
Mamoru Tobisu (2012)
10.1021/jm300037x
Structure-guided design, synthesis, and evaluation of guanine-derived inhibitors of the eIF4E mRNA-cap interaction.
X. Chen (2012)
10.1021/NP030529K
New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense.
O. B. Abdel-Halim (2004)
10.1021/CR020049I
New chiral phosphorus ligands for enantioselective hydrogenation.
Wenjun Tang (2003)
10.1016/j.bmc.2009.11.033
Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC).
Sharmila Sivendran (2010)
10.1021/la9048314
Functionalization of oxide surfaces by terpyridine phosphonate ligands: surface reactions and anchoring geometry.
Valentina Spampinato (2010)
10.1039/B500511F
Recent advances in the use of phosphorus-centered radicals in organic chemistry.
D. Leca (2005)
10.1021/OM900771V
Synthesis of Arylphosphonates via Palladium-Catalyzed Coupling Reactions of Aryl Imidazolylsulfonates with H-Phosphonate Diesters
Y. Luo (2009)
10.1021/JA00040A060
New 4+1 radical annulations. A formal total synthesis of (±)-camptothecin
D. Curran (1992)
10.1021/ol402672e
Nickel-catalyzed C-P cross-coupling of arylboronic acids with P(O)H compounds.
Gaobo Hu (2013)
10.1021/CR00044A004
Michaelis-Arbuzov rearrangement
A. Bhattacharya (1981)
10.1016/0040-4020(95)00348-C
Radical annulations and cyclisations with isonitriles: the fate of the intermediate imidoyl and cyclohexadienyl radicals
D. Nanni (1995)
10.1021/jm101035x
Discovery of a series of phosphonic acid-containing thiazoles and orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphatase.
Q. Dang (2011)
10.1039/B818618A
Tin(IV) phosphonates: porous nanoparticles and pillared materials
S. Kirumakki (2009)
10.1002/anie.201305202
Pyridine-directed palladium-catalyzed phosphonation of C(sp2)-H bonds.
C. Li (2013)
10.1021/JA003879R
Synthetic and theoretical studies on group-transfer imidoylation of organotellurium compounds. remarkable reactivity of isonitriles in comparison with carbon monoxide in radical-mediated reactions.
S. Yamago (2001)
10.1002/EJOC.201100486
Synthesis of Phosphonylated and Thiolated Indenones by Manganese(III)‐Mediated Addition of Phosphorus‐ and Sulfur‐Centered Radicals to 1,3‐Diarylpropynones
J. Zhou (2011)
10.1021/cc100101a
Generation of diverse 2H-isoindol-1-ylphosphonates via three-component reaction of 2-alkynylbenzaldehyde, aniline, and phosphite.
X. Yu (2010)



This paper is referenced by
10.1007/s10593-018-2261-7
Transition metal-promoted reactions of diarylphosphine oxides as a synthetic method for organophosphorus heterocyclic compounds
Y. Budnikova (2018)
10.1039/c7ob02221b
Microwave-assisted synthesis of hydroxyl-containing isoquinolines by metal-free radical cyclization of vinyl isocyanides with alcohols.
Dengqi Xue (2017)
10.1021/ol5013839
Silver-catalyzed synthesis of 3-phosphorated coumarins via radical cyclization of alkynoates and dialkyl H-phosphonates.
Xia Mi (2014)
10.1039/c8ob02151a
Iron(iii)-catalyzed radical α,β-aminophosphinoylation of styrenes with diphenylphosphine oxides and anilines.
Y. Wang (2018)
10.1021/ol500923t
Arylative cyclization of 2-isocyanobiphenyls with anilines: one-pot synthesis of 6-arylphenanthridines via competitive reaction pathways.
Z. Xia (2014)
10.1002/ADSC.201600001
Silver‐Catalyzed Direct C${{_{sp{^{2}}}}}$H Phosphorylation of Indoles Leading to Phosphoindoles
Wangbin Sun (2016)
10.1021/ol500277u
The benzoyl peroxide promoted dual C-C bond formation via dual C-H bond cleavage: α-phenanthridinylation of ether by isocyanide.
L. Wang (2014)
10.1021/acs.joc.7b00343
Synthesis of Cyano-Containing Phenanthridine Derivatives via Catalyst-, Base-, and Oxidant-Free Direct Cyanoalkylarylation of Isocyanides.
Weihong Song (2017)
10.1021/acs.orglett.5b00197
Synthesis of 6-(arylthio)phenanthridines by copper-catalyzed tandem reactions of 2-biaryl isothiocyanates with diaryliodonium salts.
Weisi Guo (2015)
10.1039/C6RA11426A
Synthesis of 3-phosphinoylquinolines via a phosphinoylation–cyclization–aromatization process mediated by tert-butyl hydroperoxide
P. Zhang (2016)
10.1016/J.TET.2015.04.117
Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds
X. Pan (2015)
10.1021/acs.joc.7b01447
Radical Addition/Insertion/Cyclization Cascade Reaction To Assemble Phenanthridines from N-Arylacrylamide Using Cyano as a Bridge under Photoredox Catalysis.
Y. Yu (2017)
10.1039/c4cc10267c
Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines.
H. Zhang (2015)
10.1002/ADSC.201400759
Silver(I)-Mediated CH Amination of 2-Alkenylanilines: Unique Solvent-Dependent Migratory Aptitude
S. Youn (2015)
10.1039/c5cc01904d
Copper-catalyzed tandem phosphination-decarboxylation-oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides.
Pengbo Zhang (2015)
10.1002/EJOC.201500587
Silver‐Catalyzed Aerobic Oxidative Decarboxylative Coupling of Arylpropiolic Acids with H‐Phosphine Oxides: Mild and Facile Synthesis of β‐Oxophosphine Oxides
Yao‐Fu Zeng (2015)
10.1021/acs.orglett.7b02453
Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1'H-Spiro[azirine-2,4'-quinolin]-2'(3'H)-ones.
Q. Meng (2017)
10.1039/C9GC00022D
Visible-light-induced tandem radical addition–cyclization of 2-aryl phenyl isocyanides catalysed by recyclable covalent organic frameworks
S. Liu (2019)
10.3762/bjoc.10.312
Come-back of phenanthridine and phenanthridinium derivatives in the 21st century
Lidija-Marija Tumir (2014)
10.1021/acs.joc.7b00907
Synthesis of 6-Phosphorylated Phenanthridines by Mn(II)-Promoted Tandem Reactions of 2-Biaryl Isothiocyanates with Phosphine Oxides.
Weisi Guo (2017)
10.1002/EJOC.201500988
Preparation of 6-difluoromethylphosphonated phenanthridines by visible-light-driven radical cyclization of 2-isocyanobiphenyls
S. Wang (2015)
10.1039/C4RA02381A
Synthesis of 6-aminophenanthridines via palladium-catalyzed insertion of isocyanides into N-sulfonyl-2-aminobiaryls
H. Jiang (2014)
10.1039/c6cc09430a
Organocatalyzed aerobic oxidative Robinson-type annulation of 2-isocyanochalcones: expedient synthesis of phenanthridines.
Zhongyan Hu (2017)
10.1002/ADSC.201801623
Selective C−H or N−H Imidoylative Annulation of 2‐(2‐Isocyanophenyl)‐1H‐indoles Leading to Diverse Indole‐fused Scaffolds
Fan Teng (2019)
10.1002/AJOC.201402027
Synthesis of 6-Phenanthridinephosphonates via a Radical Phosphonation and Cyclization Process Mediated by Manganese(III) Acetate
Yuzhen Gao (2014)
10.1021/acs.orglett.6b00257
Oxidative C(sp(2))-H Phosphonation of Aldehyde Hydrazones.
P. Xu (2016)
10.1039/C6QO00048G
Manganese(II)-catalyzed modular synthesis of isoquinolines from vinyl isocyanides and hydrazines
H. Mao (2016)
10.1039/C8QO00887F
Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives
X. Liu (2018)
10.1016/J.TET.2014.07.078
Silver-catalyzed 2-isocyanobiaryls insertion/cyclization with phosphine oxides: synthesis of 6-phosphorylated phenanthridines
Jia-jia Cao (2014)
10.1016/j.tetlet.2019.151278
First asymmetric enantioselective total synthesis of phenanthridine alkaloid, (S)-(+)-asiaticumine and its enantiomer
T. Nishiyama (2019)
10.1246/CL.160305
Copper-catalyzed Phosphorylation of Coumarins with Trialkyl Phosphites
S. Guo (2016)
10.1070/RCR4525
Phosphorylation of C-H bonds of aromatic compounds using metals and metal complexes
Yu H Budnikova (2015)
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