B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols

Article abstract of DOI:10.1002/adsc.202100590

We developed a B(C₆F₅)₃ catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations proceeded through the activation of phenol by B(C₆F₅)₃ with subsequent protonation of alkyne/Friedel-Crafts-type reaction. (Figure presented.).

Full text of DOI:10.1002/adsc.202100590

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doi.org/10.1002/adsc.202100590
B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with
Phenols
Jiaming Zhou,a Jin Huang,a Changhui Lu,a,* Huanfeng Jiang,a and
Liangbin Huanga,*
a
School of Chemistry and Chemical Engineering, State Key Laboratory of Pulp & Paper Engineering, South China University of
Technology, Guangzhou 510640, People’s Republic of China
E-mail: lvchh@scut.edu.cn; huanglb@scut.edu.cn
Manuscript received: May 16, 2021; Revised manuscript received: July 15, 2021;
Version of record online: ■■■, ■■■■
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.202100590
terminal alkynes with phenols, the seminal work was
Abstract: We developed a B(C6F5)3 catalyzed hy-
droarylation of terminal alkynes with various
phenols at room temperature without adding any
additives, leading to the synthesis of 2-gem-vinyl-
reported by Yamaguchi and colleagues using stoichio-
metric amount of SnCl4À NBu3 adduct.[4] Later, homo-
geneous Lewis acid such as SnCl4, GaCl3, In(OTf)3,
gold catalyst and some heterogeneous catalysts were
phenols with good regio-selectivity. Those trans-
found to be active catalyst for those transformations.[5]
formations featured a broad substrate scope with
Though a series of 2-vinyl phenol derivatives were
moderate yields. Mechanism studies indicated that
obtained in good yields through those methods, it still
those transformations proceeded through the activa-
exhibited several disadvantages including using strong
tion of phenol by B(C6F5)3 with subsequent proto-
inorganic acid, or expensive gold catalyst, high
nation of alkyne/Friedel-Crafts-type reaction.
reaction temperature, poor regioselectivity and narrow
substrate scopes.
2-Vinylphenol moiety was an important synthetic
Keywords: B(C6F5)3; 2-gem-vinylphenols; alkynes;
intermediate and widely existed in bioactive com-
phenols
pounds, such as oxyresveratrol, bervastatin, pinoxepin
(Scheme 1c).[6] Therefore, the development of efficient
and robust methods to construct 2-vinylphenol under
The CÀ H hydroarylation of alkynes was a straightfor- mild conditions from commercially available phenols
ward and atom-economical method for the synthesis of and alkynes were highly desirable.
substituted styrenes,[1a–b] which were valuable building
In recent years, electron-deficient boron-based
blocks and common structural motifs in natural catalyst systems, especially for B(C6F5)3 catalyst, had
products, pharmaceuticals, materials science.[2] In most exhibited great potential for direct CÀ H bond
transition-metal catalyzed CÀ H hydroarylation of transformations.[7–8] Zhang and co-workers reported a
alkynes, symmetrical internal alkynes or electronically B(C6F5)3 catalyzed chemoselective and ortho-selective
biased alkynes were utilized as substrates to avoid the alkylation of phenol derivatives with α-aryl
problematic regioselectivity issue or obtain the sole diazoesters.[8a] In 2019, Li group achieved the B(C6F5)3
regioselectivity due to the biased electronic property of catalyzed ortho-selective hydroarylation of 1,3-dienes
alkyne.[1c–k] Generally, terminal alkynes were less with various phenols.[8b] Interesting, Bentley and
compatible with CÀ H activation conditions, therefore, Caputo reported the B(C6F5)3-catalyzed hydroarylation
the direct hydroarylation of terminal alkynes was of alkenes and phenols with para-selectivity.[8c] In-
underdeveloped.[3] Recently, some elegant works were spired by those works, we developed a B(C6F5)3-
reported to achieve the controllable 1,2-insertion[3a–c] catalyzed hydroarylation of terminal alkyne with
and 2,1-insertion[3c–g] of terminal alkynes based on the phenols to selectively give 2-gem-vinylphenols under
radius of metal catalyst (Scheme 1a). The second route mild conditions (Scheme 1c).
was Friedel-Crafts type hydroarylation of alkyne with
We started our investigations using 4-meth-
electron-rich aromatic compounds via the electrophilic oxyphenol 1a and phenylacetylene 2a as substrates.
activation of alkynes by Brønsted or Lewis acids After extensive condition screening, we defined the
(Scheme 1b).[3h–j] For the direct hydroarylation of optimal conditions as the use of B(C6F5)3 (5 mol%) as
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94% yield (Table 1, entry 1). An array of other solvents
was less effective, especially high polarity solvent such
as DMSO, DMF or CH3CN giving no desired product
°
even at elevated 90 C (Table 1, entry 2–4). Slightly
increasing or decreasing temperature lead to a similar
outcome. However, further increasing the temperature
°
to 60 C resulted in the yield decreased to 71%
(Table 1, entries 5–7). When the reaction was per-
formed under air or with a lower catalyst loading, the
yield respectively dropped to 63% or 75% (Table 1,
entries 8–9). Other Lewis or Brønsted acid catalysts,
such as Sn(OTf)2, In(OTf)3, BF3-Et2O, BCl3 or PTSA
failed to afford the desired product (Table 1, en-
tries 10–14).
With the optimized conditions in hand, we inves-
tigated the scope of phenylacetylene derivatives
(Scheme 2). A variety of para-substituted phenylacety-
lenes were suitable substrates for those transformations
(Scheme 2, 3a–3i). It was worth mentioning that
methoxy, fluoride, chloride, bromide were tolerated,
(Scheme 2, 3e–3h) which could be further transferred
into other functional groups via
transition-metal
catalyzed
cross-coupling
Scheme 1. Direct CÀ H hydroarylation of terminal alkyne.
reactions.[9] When 1,4-diethynylbenzene was utilized
as substrates, the mono-hydroarylation product was
afforded in 46% yield (Scheme 2, 3i). Those trans-
°
catalyst, chlorobenzene as solvent at 25 C for 36 h, formations appeared insensitively to the steric hin-
which could afford the ortho-selective product 3a in drance of the phenylacetylene derivatives. ortho-,
Table 1. Optimization of reaction conditions.[a]
°
Entry
Catalyst
Solvent
Temp ( C)
Yield(%)[b]
1
2
3
4
5
6
7
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
B(C6F5)3
Sn(OTf)2
In(OTf)3
BF3-Et2O
BCl3
PhCl
toluene
DCM
25
25
25
94(82)[c]
16
88
n.d.
89
92
71
63
75
n.d.
n.d.
n.d.
n.d.
n.d.
DMSO, DMF or MeCN
25 or 90
0
PhCl
PhCl
PhCl
PhCl
PhCl
PhCl
PhCl
PhCl
PhCl
PhCl
40
60
25
25
25
25
25
25
8[d]
9[e]
10
11
12
13
14
PTSA
25
[a] Reaction conditions: 1a (0.1 mmol), 2a (0.2 mmol), catalyst (5 mol%), solvent (1 mL), under N2 for 36 h.
[b] Yields were determined by GC using dodecane as internal standard.
[c] Isolated yield in the parentheses.
[d] under air.
[e] 2 mol% catalyst was used.
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Scheme 2. Substrate scope of phenylacetylenes. reaction con-
ditions: 1a (0.5 mmol), 2 (1.0 mmol), B(C6F5)3 (5 mol%), dry
°
PhCl (5 mL), under N2, 25 C for 36 h. Isolated yield.
meta-, and multi-substituted phenylacetylenes were
converted into the desired products in moderate yields
(Scheme 2, 3j–3m). The naphthalene and thiophene
derivatives were compatible during those transforma-
tions (Scheme 2, 3n–3p). The aliphatic substituted
terminal alkynes and internal alkynes were nonreactive
under the standard conditions. Subsequently, we
continued to evaluate the substrate scope with regard
to the phenols. For less electron-rich phenol substrates,
10 mol% B(C6F5)3 and longer reaction time was
needed to assurance a good yield (see supporting
information for details). Simple phenol was ortho-
Scheme 3. Substrate scope of phenols.
alkenylated in 33% yield (Scheme 3, 3q). Halide (Scheme 4). 2-gem-Vinylphenol 3a was obtained with
(Scheme 3, 3r–3u), benzyl (Scheme 3, 3v), thioether 1.75 g in a 15 mmol scale reaction without further
(Scheme 3, 3w), allyl group (Scheme 3, 3za) were optimization. The synthetic utilities of 2-gem-vinyl-
well compatible in those transformations. It was glad phenol moiety were demonstrated by one-step con-
to obtain the selective ortho-substituted products and versions of 3a into versatile functional molecules such
no para-substituted by-products were detectable as coumarin derivative in 71% yield,[10] diaryl ether in
(Scheme 3, 3x--3za). Multi-substituted phenols, 1- 54% yield,[11] benzofuran in 74% yield.[12]
naphthol, 2-naphtholderivatives were all transferred
into desired products in good yields (Scheme 3, 3zb– to explore the mechanism (Scheme 5 eq 1–2). The
3zi). hydroarylation did not occur at all when 1,4-dimeth-
Finally, several control experiments were conducted
The robustness and potential applications of the oxybenzene 1a’ was utilized to displace 4-meth-
B(C6F5)3-catalyzed hydroarylation of phenols with oxyphenol as the substrate. It clearly supported the
terminal alkynes was demonstrated by the gram-scale critical role of hydroxyl group of phenol in those
reaction and several follow-up transformations transformations.[8b] Subsequently, when 2,6-disubsti-
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Scheme 4. Applications of B(C6F5)3 catalyzed hydroarylation.
Conditions a: 3a (0.5 mmol), Pd(OAc)2 (7.5 mol%), Cs2CO3
°
(1.5 mmol), diglyme (5.0 ml), 100 C for 18 h, under CO2.
Conditions b: 3a (0.5 mmol), KOtBu (1.1 equiv.), Ph2IOTf
Scheme 6. Plausible mechanism.
°
(1.2 equiv.), THF (2.0 ml), 25 C for 24 h, under N2. Conditions
c: 3a (0.4 mmol), Ni(acac)2 (5 mol%), PPh3 (10 mol%),
TEMPO (10 mol%), DMA (1 mL), 140 C for 36 h, under 1 atm
°
to the phenol anion to afford the dearomatized
intermediate III. Rearomatization of III followed by
the dissociation of B(C6F5)3 provided the desired
product and regenerated the catalyst.
of O2.
In summary, we presented a B(C6F5)3-catalyzed
intermolecular hydroarylation of terminal alkynes with
phenols to construct 2- vinylphenols. Those trans-
formations exhibited mild reaction conditions, high
yields, and a broad substrate scope. Moreover, this
protocol offered practical access to diverse ortho-
alkenyl phenols, which were versatile building blocks
for subsequent chemical transformations.
Experimental Section
Scheme 5. Control experiments.
In a nitrogen glovebox, the mixture of 4-methoxyphenol 1a
(0.5 mmol, 62 mg), B(C6F5)3 (5 mol%, 12.5 mg) and ethynyl-
benzene 2a (1 mmol, 102 mg) were dissolved in 5 mL
anhydrous chlorobenzene in a 20-mL Schlenk tube with a
magnetic stir bar. The Schlenk tube was taken out of the
tuted phenol 1b’ was applied as substrate, no para-
hydroarylation product was formed, which further
supported the high ortho-selectivity of those trans-
formations. The hydroxyl peak of 1a shifted from
4.83 ppm to 5.81 ppm after adding equivalent amount
of B(C6F5)3 to the system (see supporting information
for details). B(C6F5)3 acted as Lewis acid to activate
the hydroxyl group and increased the acidity of
phenol,[8b] which was beneficial to the protonation of
terminal alkyne and followed by the ortho Friedel-
Crafts-type addition of phenol.
°
glovebox and the reaction mixture was stirred at 25 C for 36 h
to complete the reaction (monitoring the reaction by TLC).
Then, 5 mL of brine was added to the reaction mixture and the
aqueous layer was extracted with Et2O (3×5 mL). The
combined organic layer was dried over Na2SO4 and then
concentrated in vacuo to afford the crude product. This crude
material was purified by chromatography to afford the desired
product 3a.
For further details (NMR spectra, optimization and substrate
isolation) please see the supporting information.
On the basis of previous work[7–8] and our control
experiment results, we tentatively proposed a plausible
mechanism (Scheme 6). Coordination of the phenol to
B(C6F5)3 generated the Lewis adduct I. Then proton
transferred from the phenolic OÀ H group to the alkyne
formed an ion-pair intermediate II, which were
followed by the electrophilic attack of the carbocation
Acknowledgements
The financial support of the State Key Laboratory of Pulp and
Paper Engineering (2020 C02), National Natural Science
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Foundation of China (No. 21971074, 22001076), Natural
Science Foundation of Guangdong Province (No.
2019A1515010006) and the Fundamental Research Funds for
the Central Universities (2019JQ04) is gratefully acknowl-
edged.
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B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with
Phenols
Adv. Synth. Catal. 2021, 363, 1–7
J. Zhou, J. Huang, C. Lu*, H. Jiang, L. Huang*