Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes

Article abstract of DOI:10.1002/ejoc.201901082

A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to form 1,1-diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron-rich arene, employs readily available starting m

Full text of DOI:10.1002/ejoc.201901082

A Journal of
Accepted Article
Title: Gold-Catalyzed Friedel–Crafts-like Reaction of Benzylic Alcohols
to Afford 1,1-Diarylmethanes
Authors: James V. Oakley, Tyler J. Stanley, Kate A. Jesse, Amanda K.
Melanese, Araceli A. Alvarez, Aloha L. Prince, Stephanie E.
Cain, Anna G. Wenzel, and Robert G. Iafe
This manuscript has been accepted after peer review and appears as an
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201901082
Link to VoR: http://dx.doi.org/10.1002/ejoc.201901082
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10.1002/ejoc.201901082
European Journal of Organic Chemistry
COMMUNICATION
Gold-Catalyzed Friedel–Crafts-like Reaction of Benzylic Alcohols
to Afford 1,1-Diarylalkanes
James V. Oakley,[a] Tyler J. Stanley,[a] Kate A. Jesse,[b] Amanda K. Melanese,[a] Araceli A. Alvarez,[a]
Aloha L. Prince,[a] Stephanie E. Cain,[a] Anna G. Wenzel,*[b] and Robert G. Iafe*[a]
Abstract:
A
gold-catalyzed, Friedel–Crafts-like benzylation of
operationally simple and efficient gold-catalyzed Friedel–Crafts
strategy for the benzylation of unactivated benzylic alcohols, with
high yields (up to 99%) in only 90 min at 50 C using near-
stoichiometric quantities of arene.
unactivated benzylic alcohols to form 1,1-diarylalkanes has been
developed. The operationally convenient method uses only 1.3
equivalents of the electron-rich arene, employs readily available
starting materials, is highly reproducible, and is tolerant of moisture.
Moderate-to-high product yields (34–99%) with excellent
regioselectivity were obtained. In particular, the intramolecular
arylation of benzylic alcohols to afford substituted fluorenes
represents a new avenue for gold research.
Results and Discussion
In continuation of our work investigating gold catalysis under
microwave irradiation,13 we report herein a straightforward and
cost-effective synthesis of 1,1-diarylalkanes. We began our
investigation with indanol and phenol (4 equiv) as the model
substrates in the presence of 5 mol% each Ph3PAuCl and AgSbF6
precatalyst in tetrahydrofuran at 50 oC (Scheme 1). To our delight,
the reaction proceeded smoothly to afford product 3a in moderate
yield (68%), as confirmed by NMR.
Introduction
Applications of 1,1-diarylalkanes and their syntheses have
attracted significant interest within the past few decades.1 The
1,1-diarylalkane moiety is a prevalent constituent of medicinally
relevant compounds,2 supramolecular systems,3 and synthetic
receptors.4 Cyclic derivatives of these molecules—fluorenes—
have unique properties in materials science, pharmaceuticals,
and organic synthesis.5 The Friedel–Crafts alkylation reaction
represents one of the most accessible and widely used methods
to obtain these compounds.6 Seminal work by Beller and
coworkers in 2006 utilized HAuCl4 (10 mol%) for the Friedel–
Crafts type benzylation of arenes and heteroarenes.7 The use of
1-phenylethyl acetate as the benzylating agent at 80 C for 20 h
was needed for best results. While benzyl alcohol and 4-
methoxybenzyl methyl carbonate were also investigated as
benzylating agents, the yields obtained were moderate: 60% and
59%, respectively. Beller was able to successfully employ primary
benzylic alcohols in the direct Friedel−Crafts benzylations of
neutral and activated arenes using FeCl3 (10 mol%).8 Rueping
and co-workers could effect this transformation with lower
loadings (1 mol%) using Bi(OTf)3.9 However, these methods
generally required prolonged heating and a large excess of arene
to attain high yields.
Scheme 1. Synthesis of 4-(2,3-dihydro-1H-inden-1-yl)phenol, 3a.
With this promising result, we proceeded to optimize the
reaction, investigating the effects of the solvent, temperature,
halide scavenger, and catalyst used. These results are
summarized in Table 1. The highest yields were obtained using
dichloroethane (DCE) as the reaction solvent. Increasing the
reaction temperature resulted in lower yields. Lowering the
catalyst loading to 2 mol% gold catalyst (entry 9) also had
deleterious effects on the reaction yields obtained. The use of
AgSbF6 as the halide scavenger afforded the best results. No
starting material conversion was observed in the absence of
either the halide scavenger (entry 13) or the gold(I) salt (entry 14),
indicating that an activated gold complex is necessary for product
formation. This reaction was attempted using catalytic amounts of
Brønsted acids (entries 15–17) in DCE, but poor-to-negligible
conversion to product was observed in these cases. Also, the
addition of 2,6-lutidine (entry 18) as a sterically hindered acid
scavenger resulted in no remarkable decrease in reaction yield.
The reaction of different nucleophiles with either indanol
(1a) or 1,2,3,4-tetrahydro-1-naphthol (1b) in the presence of
Ph3PAuCl/AgSbF6 (5 mol%) was investigated. As shown in Table
2, electron-rich mono- and disubstituted arenes performed well,
affording the complete conversion of starting material to product.
Isolated yields for the reactions using monosubstituted arenes
(entries 1–4) indicated that these reactions favored the para
position, as no ortho products were isolated or visible via 1H NMR.
Friedel–Crafts alkylation strategies have recently been
utilized as key C–C bond-forming steps in the total synthesis of
bioactive compounds.10 Current reports have utilized
ferroceniumboronic acid in hexa-fluoroisopropanol11 and
XtalFluor-E12 as air- and moisture-tolerant reaction catalyst
systems for this transformation. Herein, we describe an
[a]
[b]
Department of Chemistry and Biochemistry
California State University San Marcos
333 S. Twin Oaks Valley Rd, San Marcos, CA 92096 USA
E-mail: riafe@csusm.edu
http://faculty.csusm.edu/riafe
Keck Science Department, Claremont McKenna, Pitzer, and Scripps
Colleges, 925 N. Mills Ave, Claremont, CA 91711 USA
E-mail: awenzel@kecksci.claremont.edu
Supporting information for this article is given via a link at the end of
the document.
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10.1002/ejoc.201901082
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COMMUNICATION
The ortho position of the more electron-releasing substituents
was favored in reactions using disubstituted arenes (entries 5–9).
Yields tended to increase as more equivalents of the nucleophile
were added, which agrees with the reactivity patterns typically
observed with classical Friedel–Crafts alkylations.14 Only a single
alkylation occurred in the reaction of sesamol (entry 10). For the
reaction of 2-naphthol, a 98% yield of monosubstituted products
3g and 3h (5:1, respectively) was isolated as an inseparable
mixture (entry 11).
Table 2. Investigation of the reaction of benzylic alcohols with arenes.[a]
Entry
ArH
Equiv.
Product
Yield
(%)[b]
Table 1. Optimization of the reaction conditions.[a]
1
2
3
4
phenol
phenol
anisole
anisole
1.3
4
86
91
54
77
1.3
4
Entry
1
Catalyst
Solvent
THF
Temp (oC)
50
Yield (%)[b]
4-methyl-
anisole
5
6
1.3
4
87
87
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgSbF6
Ph3PAuCl/AgOTf
Ph3PAuCl/AgNO3
Ph3PAuCl/AgNTf2
Ph3PAuCl
68
22
71
4-methyl-
anisole
2
THF
90
3
toluene
toluene
xylenes
xylenes
DCE
50
[c]
4
90
–
4-methyl-
anisole
7
1.3
68
5
50
78
2[d]
91
43
56[e]
10
10
68
6
90
4-t-butyl-
phenol
8
9
1.3
4
86
93
7
50
8
DCE
90
4-t-butyl-
phenol
9
DCE
50
10
11
12
13
14
15
16
17
DCE
50
10
sesamol
4
98
DCE
50
DCE
50
[f]
DCE
50
–
98
(5:1)[c]
11
2-naphthol
1.3
[f]
AgSbF6
DCE
50
–
[c]
MeOH/AcCl
DCE
50
–
[f]
CF3CO2H
DCE
50
–
[a] Reactions were carried out with alcohol (0.4 mmol), arene (0.53 or 1.6
mmol), dichloroethane (2 mL), Ph3PAuCl (5 mol%), and AgSbF6 (5 mol%).
[b] Isolated yield after silica gel chromatography. [c] 3g:3h determined by 1H
NMR.
TfOH
DCE
50
27[g]
89
Ph3PAuCl/AgSbF6
2,6-lutidine
18
DCE
50
[a] Reactions were carried out with indanol (0.4 mmol), phenol (1.6 mmol),
catalyst/co-catalyst (5 mol%), solvent (2 mL), 90 min. [b] Isolated yield after
silica gel chromatography. [c] No product detected. [d] 34% yield of ortho
product isolated. [e] Catalyst/co-catalyst = 2 mol%. [f] No starting material
conversion observed. [g] Yield determined by GC.
The substituents on 1-phenylethanol were varied to
investigate the scope of the electrophile tolerated in the gold-
catalyzed, Friedel–Crafts-like reaction, using 4-methylanisole as
the nucleophile (Table 3). The 4-methylanisole was suitably
reactive such that only 1.3 equiv was needed in all reactions. It
was found that weakly electron-donating (entry 2) and electron-
withdrawing (entries 3–5) electrophiles afforded similar yields.
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The strongly electron-donating methoxy group resulted in a
surprisingly low yield, perhaps undergoing secondary reactions
that decomposed the reaction product. The introduction of
substitution at the ortho position also had a negative effect on
reaction performance (entry 7), presumably due to steric
hindrance. Strong electron-withdrawing groups, acting through
resonance or inductive effects (entries 8 and 9, respectively),
were found to be completely unreactive.
catalyzed intramolecular arylation represents an excellent route
to access this valuable compound class.
Table 4. Intramolecular, gold-catalyzed Friedel–Crafts-like reaction to afford
substituted fluorenes.[a]
Table 3. Scope of the gold-catalyzed Friedel–Crafts-like reaction of 4-
methylanisole with benzylic alcohols.[a]
Entry
R1
R2
Ph
CH3
H
Temp (oC)
Conc. (M)[b]
0.1
Yield (%)[c]
1
2
3
4
Ph
CH3
CH3
H
50
50
50
80
90
98
93
72
0.1
0.02
Entry
R1
R2
H
Product
5a
Yield (%)[b]
H
0.02
1
2
3
4
5
6
7
8
9
H
99
94
97
90
81
34
84
[a] Reactions were carried out with alcohol, dichloroethane, Ph3PAuCl (5
mol%), and AgSbF6 (5 mol%). [b] Concentration based on 6a–d. [c] Isolated
yield after silica gel chromatography.
CH3
F
H
5b
H
5c
Cl
H
5d
Control experiments were conducted to investigate the
mechanism of the catalytic system. First, deuterium labeling
experiments for the reaction of 4a-d1 with 4-methylanisole using
our optimized reaction conditions (Scheme 2a) resulted in 100%
retention of the deuterium at C1. Second, to determine the
secondary kinetic isotope effect (KIE), a competition experiment
was performed using equimolar quantities of 4a and 4a-d1. The
Br
H
5e
OCH3
H
H
5f
CH3
H
5g
[c]
NO2
CF3
5h
–
1H-NMR analysis of the resulting 5a showed a normal

[d]
H
5i
–
secondary KIE, kH/kD = 1.26 (Scheme 2b).21 Third, different para-
substituted alcohols (4b, 4c, 4d, and 4f) were used to establish a
Hammett equation. A plot of log(kX/kH) against the Hammett
constant σp showed decent linearity for 4a−4d. The negative
slope (ρ = −0.41) can be qualitatively interpreted in terms of a
developing positive charge in the rate-determining step.22
[a] Reactions were carried out with alcohol (0.4 mmol), 4-methylanisole (0.53
mmol), dichloroethane (2 mL), Ph3PAuCl (5 mol%), and AgSbF6 (5 mol%).
[b] Isolated yield after silica gel chromatography. [c] Starting material
decomposition observed. [d] No starting material conversion observed.
Having established an efficient and simple gold-catalyzed
intermolecular benzylation of arenes, we decided to extend this
methodology to include an intramolecular version, as this would
lead to substituted fluorenes, which have been shown to be
valuable scaffolds for blue organic/polymer light-emitting diodes
(O/PLEDs).15 Despite the broad utility of fluorenes, relatively few
synthetic approaches have been reported, to date.16–20 These
methods have utilized Brønsted and Lewis acid catalysis,16
niobium catalysis,17 palladium-catalyzed C-H activation,18 and
rhodium catalysis.19 It should be noted that gold(I) carbenes have
previously been employed to prepare substituted fluorenes.20
However, this method uses 2-cycloheptatrienyl-substituted
biphenyl precursors, which lacks the atom economy of a Friedel–
Crafts-type approach. When the biphenyl derivatives 6a–d were
reacted using Ph3PAuCl/AgSbF6 (5 mol%), the corresponding
substituted fluorenes 7a–d were isolated in excellent yield (Table
4). Given the low catalyst loading and mild reaction conditions, as
well as the generally good functional group tolerance, the gold-
Scheme 2. Mechanistic study.
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Lastly, the reaction of (R)-()-1-indanol with phenol (1.3 equiv)
was probed to investigate arylation stereochemistry. Interestingly,
the product (S)-3a was isolated in 99% ee, establishing that the
stereochemical configuration of the starting benzylic alcohol was
retained in this experiment. Further mechanistic studies of
benzylic alcohol activation by gold complexes are under
investigation, and will be discussed in a subsequent report.
Our optimized reaction conditions were employed in a
model synthesis to illustrate the synthetic utility of 1,1-
diarylalkanes (Scheme 3). Structural motifs similar to 8 have
shown activity against P388 murine lymphocytic leukemia.23
Starting from sesamol, the 1,1-diarylethane 8 was readily
prepared from 4b in 99% isolated yield.
Keywords: Alcohols • Diarylalkanes • Electrophilic substitution •
Fluorene synthesis • Gold
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Acknowledgments
We thank CSUSM for support of this research. J. Oakley was
supported by a summer research grant from Viasat. A. Melanese
was supported by a summer research grant from ACS Division of
Organic Chemistry. A. Alvarez was supported through the TRIO
McNair Postbaccalaureate Program. A. Wenzel and K. Jesse
were supported by NSF #1566124.
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Entry for the Table of Contents
COMMUNICATION
Gold catalysis, diarylalkanes
James V. Oakley, Tyler J. Stanley, Kate
A. Jesse, Amanda K. Melanese, Araceli
A. Alvarez, Aloha L. Prince, Stephanie
E. Cain, Anna G. Wenzel,* and Robert
G. Iafe*
A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to
form 1,1-diarylalkanes has been developed. The operationally convenient method
uses only 1.3 equivalents of electron-rich arene, employs readily available starting
materials, is highly reproducible, and is tolerant to moisture. Moderate-to-high
product yields (34–99%) with excellent regioselectivity were obtained.
Page No. – Page No.
Gold-Catalyzed Friedel–Crafts-like
Reaction of Benzylic Alcohols to
Afford 1,1-Diarylalkanes
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