Home / Articles / Syntheses of polyfunctional aromatic compounds from non-aromatic precursors

Syntheses of polyfunctional aromatic compounds from non-aromatic precursors

Thomas Mies 1
Thomas Mies
, 
Tsz-Kan Ma 1
Tsz-Kan Ma
, 
Anthony G. M. Barrett 1
Anthony G. M. Barrett
1 Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, UK
10.1070/RCR4931
Published 30 November 2019
Review , RCR4931, Volume 89, Issue 9, 917-965
8
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Mies T., Ma T., Barrett A. G. M. Syntheses of polyfunctional aromatic compounds from non-aromatic precursors // Russian Chemical Reviews. 2019. Vol. 89. No. 9. pp. 917-965.
GOST all authors (up to 50)
Copy cite
Mies T., Ma T., Barrett A. G. M. Syntheses of polyfunctional aromatic compounds from non-aromatic precursors // Russian Chemical Reviews. 2019. Vol. 89. No. 9. pp. 917-965.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR4931
UR - https://rcr.colab.ws/publications/10.1070/RCR4931
TI - Syntheses of polyfunctional aromatic compounds from non-aromatic precursors
T2 - Russian Chemical Reviews
AU - Mies, Thomas
AU - Ma, Tsz-Kan
AU - Barrett, Anthony G. M.
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 917-965
IS - 9
VL - 89
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2019_Mies,
author = {Thomas Mies and Tsz-Kan Ma and Anthony G. M. Barrett},
title = {Syntheses of polyfunctional aromatic compounds from non-aromatic precursors},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4931},
number = {9},
pages = {917--965},
doi = {10.1070/RCR4931}
}
MLA
Cite this
MLA
Copy cite
Mies, Thomas, et al. “Syntheses of polyfunctional aromatic compounds from non-aromatic precursors.” Russian Chemical Reviews, vol. 89, no. 9, Nov. 2019, pp. 917-965. https://rcr.colab.ws/publications/10.1070/RCR4931.
Views / Visits / Downloads
41 / 40 / 13

Keywords

Anilines
Aromatization
Benzene
Cyclotrimerization
Diels-Alder
Electrocyclization
Phenols
Ring-Closing Metathesis
Transition Metal Catalysis

Abstract

Syntheses of polyfunctional benzene derivatives from both cyclic and acyclic non-aromatic precursors are reviewed. Such aromatizations include transformations that use Diels--Alder reactions, transition metal-catalyzed reactions, base mediated aldol or Michael addition reactions or electrocyclic and pericyclic reactions. This review is limited to research that has been published since the last reviews in 2006, 2008, 2015 and 2018 and is specifically focused on aromatic and heteroaromatic compounds synthesized by construction of the benzene ring. It excludes heterocyclic compounds that lack a monocyclic benzene core. Applications of such aromatization reactions for the total syntheses of natural products as well as potential medicinal chemical entities are included.

The bibliography includes 155 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones
Liu X., Chen J., Ma T.
Organic and Biomolecular Chemistry , 2018
4.
Catalytic dehydrogenative aromatization: an alternative route to functionalized arenes
Girard S.A., Huang H., Zhou F., Deng G., Li C.
Organic Chemistry Frontiers , 2015
5.
Dehydrogenation of polycyclic hydroaromatic compounds
Fu P.P., Harvey R.G.
Chemical Reviews , 1978
11.
Intramolecular [4+2] Cycloaddition Reactions of Conjugated Enynes
Danheiser R.L., Gould A.E., de la Pradilla R.F., Helgason A.L.
Journal of Organic Chemistry , 1994
12.
The hexadehydro-Diels–Alder reaction
Hoye T.R., Baire B., Niu D., Willoughby P.H., Woods B.P.
Nature , 2012
13.
Die Hexadehydro-Diels-Alder-Reaktion: Ein Meilenstein der Arinchemie
Holden née Hall C., Greaney M.F.
Angewandte Chemie , 2014
14.
The Hexadehydro-Diels-Alder Reaction: A New Chapter in Aryne Chemistry
Holden née Hall C., Greaney M.F.
Angewandte Chemie - International Edition , 2014
15.
Methodology and applications of the hexadehydro-Diels–Alder (HDDA) reaction
Diamond O.J., Marder T.B.
Organic Chemistry Frontiers , 2017
16.
Diels-Alder Reaction in the Synthesis of Fluorinated (Hetero)Aromatic Compounds
Kondratov I.S., Tolmachova N.A., Haufe G.
European Journal of Organic Chemistry , 2018
17.
The Diels-Alder Reaction for the Synthesis of Polycyclic Aromatic Compounds
Dyan O.T., Borodkin G.I., Zaikin P.A.
European Journal of Organic Chemistry , 2019
20.
Benzannulation of Triynes to Generate Functionalized Arenes by Spontaneous Incorporation of Nucleophiles
Karmakar R., Yun S.Y., Chen J., Xia Y., Lee D.
Angewandte Chemie - International Edition , 2015
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
26.
Transition-metal-catalyzed alkyne cyclizations. A cobalt-mediated total synthesis of dl-estrone
Funk R.L., Vollhardt K.P.
Journal of the American Chemical Society , 1980
27.
Aromatic benzene compounds from acyclic precursors
Bamfield P., Gordon P.F.
Chemical Society Reviews , 1984
28.
Ring-Closing Metathesis as a Basis for the Construction of Aromatic Compounds
Donohoe T.J., Orr A.J., Bingham M.
Angewandte Chemie - International Edition , 2006
29.
Benzannulation
Kotha S., Misra S., Halder S.
Tetrahedron , 2008
32.
One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products
Kashinath K., Srinivasa Reddy D.
Organic and Biomolecular Chemistry , 2015
33.
1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles
Aguilar E., Sanz R., Fernández-Rodríguez M.A., García-García P.
Chemical Reviews , 2016
35.
Transition metal mediated carbonylative benzannulations
Song W., Blaszczyk S.A., Liu J., Wang S., Tang W.
Organic and Biomolecular Chemistry , 2017
37.
Total synthesis of clostrubin
Yang M., Li J., Li A.
Nature Communications , 2015
38.
Sequential Enyne-Metathesis/Diels-Alder Strategy: Rapid Access to Sugar-Oxasteroid-Quinone Hybrids
Sayyad A.A., Kaliappan K.P.
European Journal of Organic Chemistry , 2017
42.
Total Synthesis of Naphterpin and Marinone Natural Products
Murray L.A., Fallon T., Sumby C.J., George J.H.
Organic Letters , 2019
45.
Development of a microwave-assisted sustainable conversion of furfural hydrazones to functionalised phthalimides in ionic liquids
Karaluka V., Murata K., Masuda S., Shiramatsu Y., Kawamoto T., Hailes H.C., Sheppard T.D., Kamimura A.
RSC Advances , 2018
46.
Synthesis of Renewable meta ‐Xylylenediamine from Biomass‐Derived Furfural
Scodeller I., Mansouri S., Morvan D., Muller E., de Oliveira Vigier K., Wischert R., Jérôme F.
Angewandte Chemie , 2018
47.
Synthesis of Renewable meta ‐Xylylenediamine from Biomass‐Derived Furfural
Scodeller I., Mansouri S., Morvan D., Muller E., de Oliveira Vigier K., Wischert R., Jérôme F.
Angewandte Chemie - International Edition , 2018
48.
Visible‐Light‐Induced [4+2] Annulation of Thiophenes and Alkynes to Construct Benzene Rings
Song C., Dong X., Wang Z., Liu K., Chiang C., Lei A.
Angewandte Chemie , 2019
49.
Visible‐Light‐Induced [4+2] Annulation of Thiophenes and Alkynes to Construct Benzene Rings
Song C., Dong X., Wang Z., Liu K., Chiang C., Lei A.
Angewandte Chemie - International Edition , 2019
50.
The Reaction of a Thiophene Derivative with Maleic Anhydride
Clapp D.B.
Journal of the American Chemical Society , 1939
51.
Formation of 8-Hydroxyphenanthridines by Microwave-Mediated IMDAF Reactions; Synthesis Directed towards Lycorine Alkaloids
Gulbrandsen H.S., Serigstad H., Lovell Read M., Joos I., Gundersen L.
European Journal of Organic Chemistry , 2019
52.
Transposition of Aromaticity from a Furan to a Cyclohexane Ring in Furoisoindoles During the Interaction of 3-(Furyl)allylamines with Bromomaleic Anhydride
Alekseeva K.A., Kvyatkovskaya E.A., Nikitina E.V., Zaytsev V.P., Eroshkina S.M., Shikhaliev K.S., Truong H.H., Khrustalev V.N., Zubkov F.I.
Synlett , 2020
54.
Pyrone Diels-Alder Routes to Indolines and Hydroindolines: Syntheses of Gracilamine, Mesembrine, and Δ7-Mesembrenone
Gan P., Smith M.W., Braffman N.R., Snyder S.A.
Angewandte Chemie - International Edition , 2016
55.
Synthesis of isophthalates from methyl coumalate
Kraus G.A., Wang S.
RSC Advances , 2017
57.
Modulating Reactivity and Selectivity of 2-Pyrone-Derived Bicyclic Lactones through Choice of Catalyst and Solvent
Pfennig T., Chemburkar A., Johnson R.L., Ryan M.J., Rossini A.J., Neurock M., Shanks B.H.
ACS Catalysis , 2018
58.
Improving Selectivity of Toluic Acid from Biomass-Derived Coumalic Acid
Pfennig T., Chemburkar A., Cakolli S., Neurock M., Shanks B.H.
ACS Sustainable Chemistry and Engineering , 2018
62.
Cyclic Alkyne Approach to Heteroatom‐Containing Polycyclic Aromatic Hydrocarbon Scaffolds
Darzi E.R., Barber J.S., Garg N.K.
Angewandte Chemie - International Edition , 2019
65.
Tandem aldol condensation-Diels–Alder-aromatization sequence of reactions: a new pathway for the synthesis of 2-tetralone derivatives
Abaee M.S., Doustkhah E., Mohammadi M., Mojtahedi M.M., Harms K.
Canadian Journal of Chemistry , 2016
67.
Photochemical generation and trapping of 3-oxacyclohexyne
Fan R., Wen Y., Thamattoor D.M.
Organic and Biomolecular Chemistry , 2017
68.
Total Synthesis of (−)-Merochlorin A
Brandstätter M., Freis M., Huwyler N., Carreira E.M.
Angewandte Chemie , 2019
69.
Total Synthesis of (−)‐Merochlorin A
Brandstätter M., Freis M., Huwyler N., Carreira E.M.
Angewandte Chemie - International Edition , 2019
71.
Total Synthesis of Psymberin (Irciniastatin A)
Yu J., Yang M., Guo Y., Ye T.
Organic Letters , 2019
72.
A Concise Route to Benzofused Macrolactones via Ynolides:  Cycloproparadicicol
Yang Z., Danishefsky S.J.
Journal of the American Chemical Society , 2003
79.
Toward Chromanes by de Novo Construction of the Benzene Ring
Geist E., Berneaud-Kötz H., Baikstis T., Dräger G., Kirschning A.
Organic Letters , 2019
81.
Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling
Zheng X., Liu B., Yang F., Hu Q., Yao L., Hu Y.
Organic Letters , 2020
82.
Biosynthetic and Biomimetic Electrocyclizations
Beaudry C.M., Malerich J.P., Trauner D.
Chemical Reviews , 2005
86.
Modular Construction of Fluoroarenes from a New Difluorinated Building Block by Cross-Coupling/Electrocyclisation/Dehydrofluorination Reactions
Percy J.M., Emerson H., Fyfe J.W., Kennedy A.R., Maciuk S., Orr D., Rathouská L., Redmond J.M., Wilson P.G.
Chemistry - A European Journal , 2016
87.
Amine-Triggered 6π-Electrocyclization-Aromatization Cascade of Ynedienamines
Li X., Yu H., Huang Y.
Advanced Synthesis and Catalysis , 2017
88.
A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A
Palani V., Hugelshofer C.L., Sarpong R.
Journal of the American Chemical Society , 2019
89.
Selective Synthesis of (+)-Dysoline
Coffin A., Ready J.M.
Organic Letters , 2019
92.
De Novo Synthesis of Benzannelated Heterocycles
Feierfeil J., Magauer T.
Chemistry - A European Journal , 2017
94.
Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D
Chen Y., Zhang W., Ren L., Li J., Li A.
Angewandte Chemie , 2017
95.
Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D
Chen Y., Zhang W., Ren L., Li J., Li A.
Angewandte Chemie - International Edition , 2017
96.
Ring Closing Metathesis Approach for the Synthesis of o -Terphenyl Derivatives
Karmakar S., Mandal T., Dash J.
European Journal of Organic Chemistry , 2019
98.
Rhodium(i)-catalysed intermolecular alkyne insertion into (2-pyridylmethylene)cyclobutenes
Matsuda T., Matsumoto T.
Organic and Biomolecular Chemistry , 2016
99.
Gold(i)-catalyzed dehydrogenative cycloisomerization of 1,5-enynes
Chen G., Fang W., Wei Y., Tang X., Shi M.
Chemical Communications , 2016
100.
A convenient synthesis of 1-aryl-1H-1,2,3-triazoles from aliphatic substrates
Wang Q., Shi X., Zhang X., Fan X.
Organic and Biomolecular Chemistry , 2017
101.
Gold‐Catalyzed Dehydrogenative Cycloisomerization of 1,4‐Enyne Esters to 3,5‐Disubstituted Phenol Derivatives
Chen C., Chen X., Zhang X., Wang S., Rao W., Chan P.W.
Advanced Synthesis and Catalysis , 2017
105.
Synthesis and anti-proliferative activity of allogibberic acid derivatives containing 1,2,3-triazole pharmacophore
Wu M., Wu D., Chen J., Zhao J., Gong L., Gong Y., Li Y., Yang X., Zhang H.
Bioorganic and Medicinal Chemistry Letters , 2018
107.
Rh(iii)-Catalyzed regioselective C–H [4 + 2] C-annulation of vinyl enaminones with alkynes to form polysubstituted salicylaldehydes
Zhao Y., Zheng Q., Yu C., Liu Z., Wang D., You J., Gao G.
Organic Chemistry Frontiers , 2018
108.
Iron-catalyzed regioselective cyclotrimerization of alkynes to benzenes
Gawali S.S., Gunanathan C.
Journal of Organometallic Chemistry , 2019
109.
Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
Miyagi T., Okada S., Tada N., Sugihara M., Kagawa N., Takabatake T., Toyota M.
Tetrahedron Letters , 2019
110.
Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial
Zhang Z., Zhao D., He Y., Yang Z., Gong J.
Chinese Chemical Letters , 2019
111.
Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes
Tan J., Bormann C.T., Perrin F.G., Chadwick F.M., Severin K., Cramer N.
Journal of the American Chemical Society , 2019
117.
Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐ pseudo ‐Rubriflordilactone B
Mohammad M., Chintalapudi V., Carney J.M., Mansfield S.J., Sanderson P., Christensen K.E., Anderson E.A.
Angewandte Chemie , 2019
118.
Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐ pseudo ‐Rubriflordilactone B
Mohammad M., Chintalapudi V., Carney J.M., Mansfield S.J., Sanderson P., Christensen K.E., Anderson E.A.
Angewandte Chemie - International Edition , 2019
119.
Dual Gold‐Catalyzed Cycloaromatization of Unconjugated ( E )‐Enediynes
Zamani F., Babaahmadi R., Yates B.F., Gardiner M.G., Ariafard A., Pyne S.G., Hyland C.J.
Angewandte Chemie , 2019
120.
Dual Gold‐Catalyzed Cycloaromatization of Unconjugated ( E )‐Enediynes
Zamani F., Babaahmadi R., Yates B.F., Gardiner M.G., Ariafard A., Pyne S.G., Hyland C.J.
Angewandte Chemie - International Edition , 2019
127.
Stereoselective Synthesis of Tetrahydroisoquinolines from Chiral 4-Azaocta-1,7-diynes and 4-Azaocta-1,7-enynes
Sirvent A., García-Muñoz M.J., Yus M., Foubelo F.
European Journal of Organic Chemistry , 2019
130.
Pd(OAc)2-catalyzed one-pot preparation of anthranilates from acyclic unsaturated β-enamino esters
Mikami S., Okada S., Kishimoto R., Takabatake T., Toyota M.
Tetrahedron Letters , 2020
134.
Metal-Free I2 -Catalyzed Highly Selective Dehydrogenative Coupling of Alcohols and Cyclohexenones
Liang Y., Yuan Y., Shen T., Song S., Jiao N.
Chinese Journal of Chemistry , 2018
137.
Iodine‐Mediated Synthesis of Methylthio‐Substituted Catechols from Cyclohexanones
Wu Y., Wang N., Zhang T., Yan Z., Xu B., Inoa J., Xing Y.
Advanced Synthesis and Catalysis , 2019
140.
Carbene‐Catalyzed Desymmetrization and Direct Construction of Arenes with All‐Carbon Quaternary Chiral Center
Zhu T., Liu Y., Smetankova M., Zhuo S., Mou C., Chai H., Jin Z., Chi Y.R.
Angewandte Chemie , 2019
141.
Carbene‐Catalyzed Desymmetrization and Direct Construction of Arenes with All‐Carbon Quaternary Chiral Center
Zhu T., Liu Y., Smetankova M., Zhuo S., Mou C., Chai H., Jin Z., Chi Y.R.
Angewandte Chemie - International Edition , 2019
142.
Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles
Ni Z., Mou C., Zhu X., Qi P., Yang S., Chi Y.R., Jin Z.
European Journal of Organic Chemistry , 2020
144.
Atroposelective Arene Formation by Carbene‐Catalyzed Formal [4+2] Cycloaddition
Xu K., Li W., Zhu S., Zhu T.
Angewandte Chemie - International Edition , 2019
147.
Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process
Peng F., Zhao Q., Huang W., Liu S., Zhong Y., Mao Q., Zhang N., He G., Han B.
Green Chemistry , 2019
149.
Divergent Total Syntheses of (−)-Daphnilongeranin B and (−)-Daphenylline
Chen X., Zhang H., Yang X., Lv H., Shao X., Tao C., Wang H., Cheng B., Li Y., Guo J., Zhang J., Zhai H.
Angewandte Chemie , 2017
150.
Divergent Total Syntheses of (−)-Daphnilongeranin B and (−)-Daphenylline
Chen X., Zhang H., Yang X., Lv H., Shao X., Tao C., Wang H., Cheng B., Li Y., Guo J., Zhang J., Zhai H.
Angewandte Chemie - International Edition , 2017
152.
Synthesis of: Meta-substituted anilines via a three-component reaction of acetone, amines, and 1,3-diketones
Galeev A.R., Dmitriev M.V., Mokrushin I.G., Mashevskaya I.V., Maslivets A.N., Rubin M.
Organic and Biomolecular Chemistry , 2019
157.
Total Synthesis of (−)‐Daphenylline
Xu B., Wang B., Xun W., Qiu F.G.
Angewandte Chemie , 2019
158.
Total Synthesis of (−)‐Daphenylline
Xu B., Wang B., Xun W., Qiu F.G.
Angewandte Chemie - International Edition , 2019
160.
Divergent Synthesis of 3-Hydroxyfluorene and 4-Azafluorene Derivatives from ortho-Alkynylarylketones
Laohapaisan P., Chuangsoongnern P., Tummatorn J., Thongsornkleeb C., Ruchirawat S.
Journal of Organic Chemistry , 2019
161.
Vinylogous Annulation Cascade Toward Stereoselective Synthesis of Highly Functionalized Indanone Derivatives
Bhajammanavar V., Mallik S., Baidya M.
Advanced Synthesis and Catalysis , 2019
163.
Base-promoted regioselective synthesis of 1,2,3,4-terahydroquinolines and quinolines from N-boc-3-piperidone
Shally, Althagafi I., Singhal D., Panwar R., Shaw R., Elagamy A., Pratap R.
Tetrahedron , 2019
166.
Copper-Catalyzed Acetylation of Electron-Rich Phenols and Anilines
Yan G., Huang D., Yu J., Zhang J., Ke Q., Tian F., Jiang B., Ji C., Zhang L.
Synlett , 2019
169.
Biomimetic Total Syntheses of Sanctis A–B with Structure Revision
Huo L., Dong C., Wang M., Lu X., Zhang W., Yang B., Yuan Y., Qiu S., Liu H., Tan H.
Organic Letters , 2020
171.
One‐Pot Synthesis of Metastable 2,5‐Dihydrooxepines through Retro‐Claisen Rearrangements: Method and Applications
Zhang W., Baudouin E., Cordier M., Frison G., Nay B.
Chemistry - A European Journal , 2019
172.
Asymmetric Synthesis of Biaryl Atropisomers Using an Organocatalyst‐Mediated Domino Reaction as the Key Step
Hayashi Y., Takikawa A., Koshino S., Ishida K.
Chemistry - A European Journal , 2019