Sustainable Manganese-Catalyzed C?H Activation/Hydroarylation of Imines

Article abstract of DOI:10.1002/cctc.201800144

Expedient C?H additions of heteroarenes onto aldimines were realized by a sustainable manganese catalysis manifold within a removable directing group strategy. The C?H activation features most user-friendly reaction conditions, excellent chemo- and position-selectivity as well as ample substrate scope. Detailed experimental mechanistic studies suggest an organometallic C?H manganesation mode of action.

Full text of DOI:10.1002/cctc.201800144

Accepted Article
Title: Sustainable Manganese-Catalyzed C-H Activation/Hydroarylation
of Imines
Authors: Yu-feng Liang, Leonardo Massignan, and Lutz Ackermann
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10.1002/cctc.201800144
ChemCatChem
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Sustainable Manganese-Catalyzed C–H Activation/Hydroarylation
of Imines
Yu-Feng Liang,+ Leonardo Massignan,+ and Lutz Ackermann*
Abstract: Expedient C–H additions of heteroarenes onto aldimines
were realized by a sustainable manganese catalysis manifold within
a removable directing group strategy. The C–H activation features
most user-friendly reaction conditions, excellent chemo- and
position-selectivity as well as ample substrate scope. Detailed
experimental mechanistic studies were suggestive of an
organometallic C–H manganesation mode of action.
reaction medium for site-selective C–H functionalizations at
ambient pressure; iii) synthetically useful removable[15]
pyri(mi)dyl groups, and iv) detailed mechanistic insights into the
working mode of the manganese-catalyzed C–H activation
(Scheme 1).
Introduction
Transition metal-catalyzed C–H activation[1] has emerged as an
increasingly viable tool for improving the step economy in
molecular syntheses, with transformative applications to
medicinal chemistry, material sciences and crop protection,
among others.[2] During the past decades, progress has largely
relied on complexes derived from precious 4d or 5d metals, such
as noble rhodium, iridium, or palladium.[1] However, recent focus
has shifted towards the use of earth-abundant, less toxic 3d
metal complexes as catalysts for C–H functionalizations.[3] In this
context, considerable recent advances were achieved with
sustainable organometallic manganese catalysts,[4] with key
contributions by Takai/Kuninobu,[5] Wang,[6] and Ackermann,[7]
among others.[8]
Scheme 1. Sustainable manganese-catalyzed C–H activation/ hydroarylation
of imines.
Results and Discussion
We initiated our studies by probing reaction conditions for the
envisioned manganese-catalyzed C–H activation of 1-(pyridin-2-
yl)-1H-indole
(1a)
with
N-benzylidene-4-
Given the prevalence of amines in bioactive natural products
and drugs, the direct addition of C–H bonds onto C=N double
bonds represents a powerful approach for the rapid synthesis of
methylbenzenesulfonamide (2a). We were delighted to observe
that the desired product 3aa was obtained in 47% yield,
highlighting the versatility of manganese C–H activation.
Detailed optimization studies revealed Mn2(CO)10 as the best
catalyst (entries 1-5, Table 1). A variety of different additives,
such as bases, ligands, and Lewis acids, failed to improve the
catalyst’s efficacy (entries 6-11). Polar solvents, including protic
tBuOH, proved viable for the manganese-catalyzed C–H
activation (entries 12-20). While ethereal solvents offered the
optimal performance (entries 18-20), nBu2O was selected as the
ideal reaction medium because of its higher boiling point of
142 °C, so as to avoid special high-pressure technologies.
substituted
amines.[9]
In
this
context,
expensive
pentamethylcyclopentadienyl complexes of toxic rhodium and
cobalt allowed for addition reactions of arenes onto imines.[10] In
sharp contrast, less expensive and less toxic manganese has
only recently been identified as catalyst for the position-selective
C=Het hydroarylations.[11] Despite this indisputable progress, the
manganese catalysis regime required drastic conditions with
Et2O as the solvent at a reaction temperature of 100 °C, thus
calling for high-pressure technologies and special safety
features. However, within our program on sustainable
catalysis,[12] we have now devised most user-friendly
manganese-catalyzed
site-selective
C–H
activation/hydroarylations[13] of imines with ample substrate
scope. Notable features of our findings include i) general
assembly of bioactive aminomethylated indoles, key motifs in
natural products and pharmaceuticals,[14] ii) a most user-friendly
[*]
Dr. Y.-F. Liang, L. Massignan, Prof. Dr. L. Ackermann
Institut für Organische und Biomolekulare Chemie
Georg-August-Universität Göttingen
Tammannstraße 2, 37077 Gottingen (Germany)
E-mail: Lutz.Ackermann@chemie.uni-goettingen.de
Homepage: http://www.ackermann.chemie.uni-goettingen.de/
These authors contributed equally to this work.
[+]
Supporting information for this article is given via a link at the end of
the document.
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Table 1. Optimization of manganese-catalyzed C–H activation/hydroarylation.
Entry
1
[Mn]
Additive
Solvent
Yield/%[b]
47
Mn2(CO)10
MnBr(CO)5
–
–
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
1,4-dioxane
PhMe
2
–
30
3
–
---
4
MnCl2
–
---
5
Mn(OAc)2
MnBr(CO)5
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
Mn2(CO)10
–
---
6
NaOAc
45
7
NaOAc
45
8
Cy2NH
38
9
PPh3
42
10
11
12
13
14
15
16
17
18
19
20
ZnBr2
10
BF3•OEt2
40
42[c]
–
–
–
–
–
–
–
–
–
30
DME
27
DCE
32
DMF
5
Scheme 2. Manganese-catalyzed C–H activation/hydroarylation of imines 2.
tBuOH
42
Et2O
88
iPr2O
83
nBu2O
85
The robustness of the manganese-catalyzed C–H activation
was then investigated with respect to the indole moiety 1
(Scheme 3). Hence, a broad range of synthetically useful
electrophilic groups was well tolerated, including fluoro, bromo,
nitro and ester substituents (3ba-3ja). Thereby, either electron-
donating or electron-withdrawing groups were included on the
benzoid indole motif. Further, even substituents in the indole’s
C-3 position were well accepted despite of their increased steric
hinderance (3ka-3ma). It is also notable that the manganese-
catalyzed C–H activation/hydroarylation was not limited to
indoles. Indeed, the C–H activation was also successfully
performed on the synthetically meaningful pyrrole to give the
product 3na with execllent levels of site- and mono-selectivities.
In contrast, under otherwise identical reaction conditions 3-
pyridyl-substituted furane or thiophene provided thus far less
satisfactory results.
[a] Reaction conditions: 1a (0.50 mmol), 2a (1.00 mmol), [Mn] (10 mol %),
additive (20 mol %), solvent (1.0 mL), at 100 °C for 24 h. [b] Isolated yield. [c]
120 °C. DME = 1,2-dimethoxyethane; DCE = 1,2-dichloroethane; DMF = N,N-
dimethylformamide.
With
activation/hydroarylation in hand, we tested its versatility with
differently substituted imines (Scheme 2). The robust
the
optimized
manganese-catalyzed
C–H
2
manganese catalyst proved to be tolerant of various functional
groups, such as methoxy, chloro, trifluoromethyl, nitro, and
bromo substituents in various positions (3aa-3al). Likewise,
synthetically useful heteroarenes, such as furane and thiophene,
were successfully converted (3am-3an). Notably, the N-
substituent on the imines 2 could be varied to even include an
aromatic moiety (3ao-3aq), provided that an alkoxycarbonyl
group was present.
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10.1002/cctc.201800144
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hydroarylations in the presence of isotopically labeled cosolvent
led to considerable H/D scrambling, highlighting a facile C–H
cleavage (Scheme 5). In good agreement with this observation,
a minor kinetic isotope effect (KIE) of only kH/kD  1.3 was
observed (Scheme 6), again indicating fast C–H activation.
Moreover, the well-defined cyclometalated complex 4[7i] was
prepared, and proved competent in a catalytic and stoichiometric
setting (Scheme 7), providing further support for complex 4
being a key intermediate of the organometallic C–H activation
manifold.
Scheme 5. H/D exchange experiment.
Scheme 3. Manganese-catalyzed C–H activation/hydroarylation of indoles 1.
Scheme 6. Kinetic isotope effect study.
Scheme 7. Cyclometalated complex 4 in catalytic and stoichiometric
reactions.
Scheme 4. Intermolecular competition experiments.
Given the high catalytic efficacy of the manganese-catalyzed
hydroarylation, we became attracted to delineating its mode of
action. To this end, competition experiments were performed,
revealing that electron-rich indoles 1 and electron-deficient
imines 2 inherently reacted faster (Scheme 4). These findings
are indicative of a rate-determining nucleophilic attack of an
organometallic manganese intermediate. Manganese-catalyzed
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Conclusions
In conclusion, we have reported on the efficient C–H
activation/hydroarylation of imines by means of inexpensive and
nontoxic manganese catalysis at ambient pressure. The
robustness of the most user-friendly manganese catalyst was
reflected by the general assembly of bioactive aminomethylated
indoles in a step-economical manner, with excellent levels of
mono-, chemo- and position-selectivities and ample scope.
Detailed mechanistic studies provided strong support for an
organometallic C–H activation manifold.
Experimental Section
Heteroarenes 1 (0.5 mmol), imines 2 (1.0 mmol), Mn2(CO)10 (19.5 mg, 10
mol %) and nBu2O (1.0 mL) were placed in a 25 mL Schlenk flask. The
mixture was stirred at 100 ºC for 24 h. After cooling to ambient
temperature, the mixture was transferred into a round bottom flask with
EtOAc (20 mL) and washed with brine (5.0 mL). The mixture was
extracted with EtOAc (3 × 20 mL) and the combined organic layer was
dried over Na2SO4, concentrated under reduced pressure and purified by
column chromatography on silica gel using a mixture of n-hexane and
EtOAc to afford the desired products 3.
Scheme 8. Proposed catalytic cycle.
Based on our mechanistic studies, we propose a plausible
catalytic cycle being initiated by a facile C–H metalation to afford
the complex 4 (Scheme 8). Coordination and subsequent
insertion lead to the seven-membered manganacycle 6.[8j,16]
Finally, intermediate 6 undergoes protonative demetalation,
delivering the desired product 3aa and regenerating the
catalytically active manganese complex 4. We suggest that the
key C–H metalation occurs by a ligand-to-ligand hydrogen
transfer (LLHT) regime.[17]
Acknowledgements
Generous support by the DFG (Gottfried-Wilhelm-Leibniz award),
and the Alexander von Humboldt Foundation (fellowship to Y.-F.
L.) is gratefully acknowledged.
Keywords: C–H activation • imine • heteroarene • manganese •
mechanism
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Entry for the Table of Contents
FULL PAPER
Y.-F. Liang, L. Massignan, L.
Ackermann*
Page No. – Page No.
Sustainable Manganese-Catalyzed C–
H Activation/Hydroarylation of Imines
Text for Table of Contents
SusMn: Manganese catalysis enabled the step-economical C–H activation/hydroarylations of aldimines with
ample scope by an organometallic C–H activation regime.
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