An atom- and pot-economical consecutive multi-step reaction approach to polycyclic aromatic hydrocarbons (PAHs)

Article abstract of DOI:10.1039/c6cc09108c

A novel one-pot benzannulation reaction has been developed for the synthesis of substituted polycyclic aromatic hydrocarbons (PAHs) from the direct coupling of propargylic aldehydes/alcohols with 1,1-diarylethanol through an atom-economical uninterrupted three/four-step reaction sequence under mild and metal-free reaction conditions. The strategy involves an acid-catalyzed dehydration and carbon-carbon bond formation followed by DBU-promoted cycloisomerization. Naphthalene and phenanthrene were obtained via mono-benzannulation, and chrysene, picene and benzopicene were obtained involving consecutive di-benzannulation reactions in good yields starting from easily accessible starting materials.

Full text of DOI:10.1039/c6cc09108c

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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
Reactivity differences of Sc3N@C2n (2n 68 and 80). Synthesis of the
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Atom- and Pot-Economical Consecutive Multi-Step Reaction
Approach to Polycyclic Aromatic Hydrocarbons (PAHs)†
Chada Raji Reddy,*a Uredi Dilipkumara and Ravula Shravyaa
Received 00th January 20xx,
Accepted 00th January 20xx
A novel one-pot benzannulation reaction has been developed for the synthesis of substituted polycyclic aromatic
hydrocarbons (PAHs) from the direct coupling of propargylic aldehydes/alcohols with 1,1-diarylethanol through an atom-
economical uninterrupted three/four-step reaction sequence under mild and metal-free reaction conditions. The strategy
involves an acid-catalyzed dehydration and carbon-carbon bond formation followed by DBU-promoted cycloisomerization.
Naphthalene and phenanthrene were obtained via mono-benzannulation and chrysene, picene and benzopicene were
obtained involving consecutive di-benzannulation reactions in good yields starting from easily accessible starting materials.
DOI: 10.1039/x0xx00000x
www.rsc.org/
The concept of atom-economy introduced by Trost is playing a same reaction conditions would lead to the formation of ene-
key role in designing the new chemical strategies, because it yne. Subsequently, addition of base in to the same reaction
seeks to maximize the synthetic efficiency in transforming the vessel would promote the cycloisomerization reaction to form
starting materials to the target molecule.1 Similarly, Pot- the benzannulated product. The process of the above
economy concept pursues the multiple transformations and consecutive multi-step reaction sequence in one-pot will lead
forming several bonds in single reaction vessel, which to a novel benzannulation approach to substituted polycyclic
minimizes the use of solvents (work-up and purification of aromatic hydrocarbons under atom-economical and metal-
intermediates) and address the chemical waste generated.2 free reaction conditions. Herein, we present the results of a
Undoubtedly, synthetic strategies following the combination novel consecutive reaction strategy for the synthesis of PAHs
of both the atom- and pot-economy are extremely attractive.
under mild conditions. To the best of our knowledge there are
Polycyclic aromatic hydrocarbon (PAH) derivatives occupy a no examples in the literature neither for the direct coupling of
significant field in organic chemistry due to their wide propargylic aldehyde with 1,1-diarylethanol (or alkene) to ene-
applications in pharmaceutical chemistry as bio-active ynes nor for the cycloisomerization of 1,4-enyne to PAHs.
molecules,3 semi-conductors and advanced organic materials.4, With this assumption, we set out to examine the reaction of
5 As a result, the construction of substituted PAH architectures propargylic aldehyde 1a and 1,1-diphenylethanol (2a) in the
has been attracted the attention of several synthetic organic presence of various acid catalysts to find the optimal
chemists. Among the methods developed for the synthesis of conditions (see supporting information, Table S1) for the
polycyclic aromatic hydrocarbons, mainly naphthalenes, formation of ene-yne through dehydration (to give
enyne-assisted cycloisomerization reactions have emerged as by nucleophilic addition (to give ). Interestingly, it provided a
one of the atom-economical reactions.6,7 These reactions di-alkenyl product
in 94% yield at 80 C in presence of pTSA
generally rely on metal-catalysis and require the pre- in CH3CN. We presume that initially the aldehyde 1a
construction of the desired ene-yne substrates.7 Hence, the underwent nucleophilic addition to
followed by immediate
development of new methods with the formation of ene-yne nucleophilic substitution with
followed by its cycloisomerization in one-pot to the target presence of acid catalyst provided
aromatic hydrocarbon under metal-free conditions, are greatly fully characterized.
desirable.
cycloisomerization reactions,8 the conversion of
A) followed
B
o
C
B
A
via carbocation in the
C
, which was isolated and
Based on earlier work on
to
C
In this direction, we hypothesized that the 1,1-diarylethanol in naphthalene was tested using DBU and found that the reaction
presence of acid-catalyst will generate the olefin, which acts as proceeded smoothly to give vinylated naphthalene 3a in 92%
a nucleophile to react with propargylic aldehyde under the yield. A plausible reaction pathway was shown in Scheme 1.
DBU promoted isomerization of C affords allene, which
undergoes 1,3,5-triene electrocyclization followed by
a.Dr. Ch. Raji Reddy, U. Dilipkumar and R. Shravya
Division of Natural Products Chemistry
aromatization leads to the benzannulation product 3a
.
Further, the reaction conditions [pTSA (5 mol%), CH3CN, 80 oC,
2h; DBU, r.t., 15 min.] were tested successfully for all the four
reactions uninterruptedly in one-pot to obtain the
naphthalene 3a in 87% yield (Table S1).
CSIR-Indian Institute of Chemical Technology
Hyderabad, 500007 (INDIA)
E-mail: rajireddy@iict.res.in.
†Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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Scheme 1: Possible reaction pathway
Scheme 2: Reaction of 2a with propargylic aldehydes
The above success prompted us to study the reaction of 2a
with various propargylic aldehydes as the reaction partner
(Scheme 2). The reaction of 1b with 2a was investigated in the
presence of acid catalyst and subsequent DBU-mediated
cycloisomerization offered 2-vinylated naphthalene 3b in 83%
yield. Similarly, other propargylic aldehydes 1c to 1g having
both electron-donating (4-Me, 2-OMe) and electron-
withdrawing substituent (4-Cl, 4-NO2, 3-CF3) on the phenyl ring Scheme 3: Scope of propargylic alcohols in benzannulation
were proved to be competent C2 synthons to generate the with 2aa
corresponding 2-vinylated naphthalenes 3c to 3g in good
yields. 3-(Thiophen-2-yl)propionaldehyde 1h worked well,
providing the product 3h in 79% yield. Remarkably, 3-(tert-
buyldimehylsilyl)-propionaldehyde 1i was also effective in
benzannulation with 2a to produce the corresponding 2-
vinylated naphthalene 3i in 90% yield with TBDMS group intact
in the product (Scheme 2).
As the formaion of intermediate
assumed through the nucleophilic substitution of propargylic
alcolhol with insitu generated nucleophile (as shown
C from propargylic aldehyde is
B
A
Scheme 1), we next investigated the feasibility of propargylic
alcohols9 as an alternative reaction partners in place of
propargylic aldehydes (Scheme 3). Firstly, the reaction of
propargylic alcohol 4a with 1,1-diphenylethanol (2a) was
examined under the optimal reaction conditions. To our
delight, one-pot benzannulation proceeded smoothly to
provide the desired naphthalene 3j in 92% yield via the enyne
D
, which was isolated and fully characterized. Noteworthy to
mention that the dehydration/propargylation were proceeded
at room temperature, while the cycloisomerization required
80 oC for faster reaction (at room temperature the reaction
time was more than 8 h). Next, the reactivity of various
propargylic alcohols using 1,1-diphenylethanol (2a) as the
reaction partner was investigated (Scheme 3). In the cases of
1-aryl propargylic alcohols (R1 = aryl), different substitutions on
2 | Chem. Commun., 2012, 00, 1-3
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the aryl ring were tolerated well. For example, p-OMe, 3,4,5- Table 1. Synthesis of PAHs via di-benzannulationa
(MeO)3 and p-Br substituted phenyl propargylic alcohols
underwent the one-pot three-step reaction smoothly to afford
the corresponding naphthalenes 3k to 3m in 80-92% yields. 1-
Heteroaryl propargylic alcohols having 3-methyl-2-thienyl and
3-indolyl substitution were also compatible in this reaction,
furnishing 3n and 3o in 87% and 90% yields, respectively.
Interestingly, 1-alkenyl substituted propargylic alcohol
(obtained by the reaction of cinnamaldehyde with phenyl
acetylene), was also suitable in reacting with 2a to afford the
expected 3p in 78% yield. The nature of R2 substitution had no
influence on the reaction, as it can be seen by the formation of
naphthalenes when R2 was aryl groups (3j to 3p) as well as
alkyl groups (3q to 3s). Notably, the propargylic alcohol having
R1 = Ph and R2 = TMS underwent the one-pot reaction well to
provide the desilylated product 3t in 80% yield.
i) pTSA (5 mol%),
CH3CN, rt, 10 min
OH
dicyclized
product
monocyclized 12 h
product
+
2a / 2g
R
ii) DBU
80 oC, 30 min
3z, 5b, 5c
4l-4n
6a - 6d
Ph
monocyclized
product
dicyclized
product
3o-alcohol
R
entry
1
Ph
Ph
2a
3z, 80 %
6a, 75 %
Ph
4l
Ph
2
4l
2g
5b, 86 %
6b, 73 %
Ph
Furthermore, the scope of 1,1-diarylethan-1-ols
2 using 1,3-
Ph
diphenylprop-2-yn-1ol (4a) as the reaction partner was also
tested (Scheme 4). In general, it was observed that 1,1-
diphenylethan-1-ols, 2b to 2f, having both of the electron-
donating (p-Me, p-MeO) as well as electron-withdrawing (p-F,
p-Cl, p-I) substitution, were successfully reacted with 4a to give
the corresponding naphthalenes 3u to 3y in good yields.
Employment of 1,1-di(naphthalene-1-yl)ethan-1-ol (2g) in the
present one-pot reaction with 4a provided substituted
phenanthrene 5a in 87% yield.
3
2g
4m
6c, 71 %
Ph
5c, 85 %
Ph
Scheme 4: Reactivity of 1,1-diarylethan-1-ols
4
R
2g
-
R = Me, 2b
R = OMe, 2c
R = F, 2d
R = Cl, 2e
R
R = I, 2f
N
Ts
OH
4n
N
Ts
R = Me, 3u, 90%
R = OMe, 3v, 85%
R = F, 3w, 92%
R = Cl, 3x, 95%
R = I, 3y, 88%
6d, 78 %
Ph
R
R
Ph
phenylchrysene (6a) in 75% yield (entry 1, Table 1). Similarly,
the reaction of 4l with 2g was also successful in providing the
double cyclization product, picene 6b in 73% yield through the
monocyclized intermediate 5b (entry 2). In addition, when we
extended the substrate scope, 1-(naphthalen-1-yl)-5-
(i) pTSA (5 mol%)
Ph
CH3CN, rt, 30-45 min
4a
(ii) DBU, 80 oC, 30-60 min
OH
phenylpenta-2,4-diyn-1-ol
benzo[a]picene 6c was isolated in 71% yield via the mono-
cyclized phenanthrene 5c (entry 3). similar one-pot
(
4m),
the
corresponding
Ph
5a, 87%
2g
Ph
A
Further, the applicability of this consecutive process was uninterrupted multi-step process was also observed to give
verified towards the synthesis of higher-membered aromatic the novel dibenzannulated product, phenanthro[1,2-
hydrocarbons such as chrysene, picene and benzopicene, c]carbazole 6d (78% yield) from the reaction of 4n with 2g
valuable motifs with numerous applications.5 In general, the
wherein we could not isolate the monocyclized product (entry
synthesis of PAHs involved the multi-step and metal-mediated 4, Table 1).
reactions.10 We assumed that the use of 2,4-diyn-1-ols in To further explore the applicability of the present method, we
reaction with 1,1-diarylethan-1-ols (Table 1) will undergo a explored the transformation of the obtained naphthalene 3s
,
.
consecutive reaction sequence involving an acid-catalyzed The alcohol group of naphthalene 3s was oxidized using IBX in
dehydration and propargylation followed by DBU-promoted acetonitrile to obtain the aldehyde, which upon treatment
double cycloisomerization (dibenzannulation) to provide the
higher-membered aromatic hydrocarbons. First, we attempted Scheme 5: Conversion of 3s to naphtho[1,2-c]carbazole 6e
the annulation of 1,5-diphenylpenta-2,4-diyn-1-ol (4l) with 2a
in the presence of pTSA followed by DBU in acetonitrile.
Gratifyingly, the formation of alkynyl-naphthalene 3z was
observed in 30 min. at 80 oC which subsequently underwent
second cyclization in 12 h at 80 oC to provide the 6-benzyl-12-
Ph
(i) IBX, CH3CN
80 oC, 2 h, 80%
3s
(ii) pTSA (10 mol%)
CH3CN, rt, 1 h, 82%
N
6e
Ts
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Suzuki, Y. Yamanari, H. Mitamura, T. Kambe, N. Ikeda, H.
Okamoto, A. Fujiwara, M. Yamaji, N. Kawasaki, Y. Maniwa
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with pTSA (10 mol%) in acetonitrile at room temperature gave
13-phenyl-7-tosyl-7H-naphtho[1,2-c]carbazoles 6e in 82% yield
(Scheme 5).
6
In summary, we have developed a simple and metal-free novel
tandem reaction for the synthesis of diverse aromatic
compounds
from
readily
accessible
propargylic
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aldehydes/alcohols and diaryl ethanols under mild reaction
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phenanthrocarbazole through the dibenzannulaion reaction.
The effectiveness of present method in the synthesis of
diversely substituted PAHs is under progress to study their
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We thank Council of Scientific and Industrial Research (CSIR),
New Delhi for financial support under XII Five Year Plan project
(ORIGIN, CSC-0108) and research fellowship to Dilipkumar.
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