Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis

Article abstract of DOI:10.1021/acs.orglett.7b01561

A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g

Full text of DOI:10.1021/acs.orglett.7b01561

Letter
pubs.acs.org/OrgLett
Phosphorylation of Alkenyl and Aryl C−O Bonds via Photoredox/
Nickel Dual Catalysis
Li-Li Liao,† Yong-Yuan Gui,† Xiao-Bo Zhang,† Guo Shen,† Hui-Dong Liu,† Wen-Jun Zhou,†,‡ Jing Li,†
and Da-Gang Yu*,†
†Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29
Wangjiang Road, Chengdu 610064, P. R. China
‡College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang 641112, P. R. China
S
* Supporting Information
ABSTRACT: A phosphorylation of alkenyl and aryl C−O bonds
at room temperature via photoredox/nickel dual catalysis is
reported. By starting from easily available and inexpensive
sulfonates, a variety of important alkenyl phosphonates and aryl
phosphine oxides are generated in moderate to excellent yields. This method features mild reaction conditions, high selectivity,
good functional group tolerance, wide substrate scope, and easy scalability.
rganic phosphorus compounds play an important role in
redox/nickel dual catalysis (Scheme 1). A variety of easily
Oorganic synthesis, medicinal chemistry, photoelectric available and inexpensive sulfonates can be transformed to
materials, and coordinative chemistry.1 Many methods have
been developed to generate such compounds. Traditionally,
Scheme 1. Phosphorylation of C(sp2)−O Bonds via
phosphorylation of organometallic reagents with electrophilic
phosphorus reagents is widely used.2 Since the 1980s, transition
metal-catalyzed cross-couplings of organohalides and carboxylic
acids with P(O)−H compounds as well as addition of P(O)-H
compounds to alkynes have emerged as efficient methods to
generate C(sp2)−P bonds.3 However, there are still some
drawbacks such as high catalyst loading, harsh reaction
conditions, and limited substrate scope as well as the use of
toxic and expensive organohalides. Therefore, the development
of more environmentally friendly methods to produce organic
phosphorus compounds is still highly desirable.
Visible-light photoredox catalysis has emerged as a powerful
and clean method to realize novel organic transformations via
unique single electron transfer (SET) process.4 Notably,
merging photoredox with transition metal catalysis5,6 shows
great potential in the cross coupling of organohalides. As
carbonyl-containing compounds and phenols exist widely and
are readily available in nature and industry, the easily generated
alkenyl and aryl C−O electrophiles are also attractive in such
dual catalysis. For example, Molander6m and Rueping6n
independently reported the novel and efficient cross couplings
of phenol derivatives with alkyl silicates or amino acids. Besides
one nice example of alkylation of enol triflates from Doyle’s
group,6o our group also contributed to this field by realizing the
direct couplings of various enol and phenol derivatives with
amine or ether C(sp3)−H bonds.6p Although C−O electro-
philes shows great potential as environmentally benign
electrophiles in such dual catalysis to form carbon−carbon
bonds, their application in formation of highly important
carbon-heteroatom bonds, including C−P bonds, has not been
realized by using this strategy. Herein, we report a novel
phosphorylation of alkenyl and aryl C−O bonds via photo-
Photoredox/Nickel Dual Catalysis
alkenyl phosphonates and aryl phosphine oxides with high
selectivity and efficiency under mild reaction conditions.
When we initiated this project, there were few examples of
C−P bond formation from other electrophiles via photoredox/
transition metal dual catalysis.6f,7 For example, Toste reported
the reaction with aryl diazonium salts as starting materials via
photoredox/gold dual catalysis.7 In the same year, the Xiao and
Lu’s group used photoredox/nickel dual catalysis strategy to
generate C−P bonds with (hetero)aryl iodides as electro-
philes.6f Both transformations are efficient; however, no alkenyl
C−P bond was formed, and the starting materials could be
unstable, toxic, difficult to prepare, and limited in scope.
Therefore, the identification of more benign coupling partners
is still of great significance in such photochemical C−P bond
construction.8 Inspired by the success in cross coupling
reactions via C(sp2)−O activation,9 especially the trans-
formation of C(sp2)−O bonds to C−P bonds,10 we
hypothesized that the mild phosphorylation of inexpensive
and readily available enol sulfonates could be realized by
merging photoredox and nickel catalysis. This method will
provide a facile route to synthesize structurally complicated
Received: May 23, 2017
© XXXX American Chemical Society
A
DOI: 10.1021/acs.orglett.7b01561
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Organic Letters
Letter
a
alkenyl phosphorus compounds, which are widely used in
organic transformations, and synthesis of drugs and ligands.11
With these in mind, we started this project by examining the
reactivity of the stable β-tetralone-derived tosylate 1a and
diethyl phosphonate 2a. After systemic screening, we were
happy to obtain the desired alkenyl phosphonate 3aa in 97%
isolated yield with 2 mol % of Ni(cod)2 as the catalyst and 5
mol % of Ru(bpy)3Cl2·6H2O as the photocatalyst (Table 1,
Scheme 2. Substrate Scope of P-Sources
a
Table 1. Reaction Conditions Optimization
a
b
Standard reaction conditions as in Table 1, entry 1. Twenty-four
hours.
b
a
entry
[Ni]
ligand
base
yield (%)
Scheme 3. Substrate Scope of Alkenyl Tosylates
1
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
Ni(cod)2
NiCl2·dppp
Ni(cod)2
−
o-phenanthroline
o-phenanthroline
o-phenanthroline
dtbbpy
DBU
Cs2CO3
DBU
DBU
DBU
DBU
DBU
−
DBU
DBU
DBU
DBU
97
<5
23
68
2
c
3
4
5
6
7
8
9
f
dppp
n.d.
dppf
<5
o-phenanthroline
o-phenanthroline
o-phenanthroline
o-phenanthroline
o-phenanthroline
−
n.d
n.d.
n.d.
trace
n.d.
96
d
10
Ni(cod)2
Ni(cod)2
Ni(cod)2
e
11
12
a
Alkenyl tosylate 1a (0.3 mmol), diethyl phosphonate 2a (0.36
mmol), Ni-catalyst (2 mol %), ligand (2 mol %), Ru(bpy)3Cl2·6H2O
(5 mol %), and base (0.6 mmol) in MeCN (0.1 M). bpy = 2,2′-
bipyridine, dtbbpy = 4,4′-di-tert-butyl-2,2′-bipyrididyl, cod = 1,5-
b
c
cyclooctadiene, LED = light-emitting diode. Isolated yield. Eosin B
d
e
was used as the photocatalyst. No Ru(bpy)3Cl2·6H2O. No light.
f
n.d., not determined.
entry 1). Switching the base to Cs2CO3 gave only trace amount
of 3aa (Table 1, entry 2), which indicated the high importance
of the base. Moreover, other photocatalysts (please refer to the
Supporting Information for more examples), nickel catalysts,
and ligands were also tested to give lower yields (Table 1,
entries 3−7). The results of control experiments performed in
the absence of a photocatalyst, a nickel catalyst, a base, or light
demonstrated the essential role of each component in this
reaction (Table 1, entries 8−11). To our surprise, the reaction
without additional ligand could also generate 3aa in 96% yield
(Table 1, entry 12). However, this finding did not prove to be
general for other substrates,12 and thus, we chose o-
phenanthroline as the ligand (Table 1, entry 1) to evaluate
the full scope of the reaction.
With the optimized reaction conditions in hand, we next
examined different P-sources (Scheme 2). The catalytic system
worked well with hydrogen phosphonates (2a−c), a hydrogen
phosphinate (2d), and phosphine oxides (2e and 2f) to give the
desired products in moderate to excellent yields, which showed
broad scope and great potential for diverse transformations.
Furthermore, we examined the scope of alkenyl tosylates
(Scheme 3). Different substituents on the arenes (1a−1d) did
not affect the reactions to give the desired products in moderate
to excellent yields. The reactions were highly chemoselective, as
C−Br13 and C−OMe9f,h bonds, which have been applied as
electrophiles in other nickel-catalysis, remained untouched,
providing potential for further transformation. Other cyclic enol
tosylates with 5−8 membered rings (1e−1h) could also
a
b
Standard reaction conditions as in Table 1, entry 1. 2a (0.45 mmol).
c
d
Twenty-four hours. Instead of o-phenanthroline, 2 mol % dtbbpy
e
f
was used. E/Z = 2:1. Diphenylphosphine oxide 2e (0.36 mmol).
undergo the C−P bond formation smoothly. Several cyclo-
hexenyl tosylates with different substituents (1i−1k) and other
kinds of cyclic enol tosylates (1l−1m) could take part in such a
reaction to give the corresponding products in moderate to
excellent yields. When we tested the reactivity of styrene
tosylate 1n, the desired product 3na was obtained in 67%, and a
trace amount of tetraethyl (1-phenylethane-1,2-diyl)bis-
(phosphonate) was detected, which might arise from the
Michael addition of 2a to 3na. It was notable that the reaction
of alkenyl tosylate 1o was highly efficient and steroselective, as
the ratio of the product isomers 3oa was the same as 1o with
full conversion. α-Tetralone derivative 1p could also generate
the desired product 3pa in high yield. However, the alkenyl
tosylates with more steric hindrance (e.g., 1,2,2-triphenylvinyl
4-methylbenzenesulfonate, (Z)-1,2-diphenylvinyl 4-methyl-
benzenesulfonate, and (Z)-1,2-diphenylprop-1-en-1-yl 4-
methylbenzenesulfonate) gave only trace amount of the
corresponding products, which might arise from the difficult
oxidative addition. Since phosphine oxides are versatile
synthetic intermediates in organic synthesis,1 we further tested
the reactions of 1p and 1q with diphenylphosphine oxide 2e to
give the desired products in moderate yields.
B
DOI: 10.1021/acs.orglett.7b01561
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Organic Letters
Letter
As aryl sulfonates and sulfamates are also readily available
from phenols and widely used as inexpensive electrophiles in
diverse cross-coupling reactions,9 we further tested them in
such C−P bond formation (Scheme 4) to replace aryl halides
Scheme 6. Mechanistic Study and Proposed Mechanism
a
Scheme 4. Substrate Scope of Phenol Derivatives
a
Reaction performed using Ru(bpy)3Cl2·6H2O (5 mol %), diphenyl-
phosphine oxide 2e (0.36 mmol), phenol derivatives 4 (0.3 mmol),
and DBU (0.6 mmol). Ni(cod)2 (2 mol %), dtbbpy (2 mol %), 3 mL
b
of DMA. Ni(cod)2 (5 mol %), o-phenanthroline (5 mol %), 3 mL of
MeCN.
the dual catalytic cycle through reduction of H by the reduced
form of Ru-photocatalyst D. However, we could not exclude
the reaction pathway including the addition of C to the E to
give a NiI complex and following oxidative addition and
reductive elimination.
In summary, we have developed an efficient phosphorylation
of alkenyl and aryl C−O bonds via photoredox/nickel dual
catalysis. This reaction showed a broad substrate scope,
excellent functional group tolerance, and easy scalability,
which afforded the alkenyl phosphonates and aryl phosphine
oxides in moderate to excellent yields.
and diazo salts.6f,7 To our delight, aryl tosylates (4a−4c)
reacted well with diphenylphosphine oxide 2e to generate the
triarylphosphine oxides 5 in excellent yields with MeCN or
N,N-dimethylacetamide (DMA) as the solvent. Besides
tosylates, a mesylate 4d and a sulfamate 4e also worked well
in this reaction.
After developing the methodology, we further demonstrated
its utility. First, the 10 mmol scale reaction of 1a under the
standard reaction conditions gave 2.4 g of the desired product
in 91% yield with similar efficiency (Scheme 5A). Second, the
ASSOCIATED CONTENT
* Supporting Information
■
S
Scheme 5. Gram-Scale Reaction and Application
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.or-
glett.7b01561.
Experimental procedures, characterization of all products
(PDF)
AUTHOR INFORMATION
■
Corresponding Author
*E-mail: dgyu@scu.edu.cn
ORCID
products could be easily transformed to other derivatives.14 For
example, phosphine oxide 3ae′ could be easily obtained in 79%
yield through the phosphorylation of 1a with 2e and following
facile reduction of the phosphine oxide 3ae (Scheme 5B).15
We next sought to gain insight into reaction mechanism.
When 1.5 equiv of 2,2,6,6-tetramethylpiperding-1-oxyl
(TEMPO) was added under the standard conditions, a trace
amount of desired product 3aa was detected (Scheme 6A),
which demonstrated that the radical might be involved in this
system. On the basis of our exploration6c,p and previous
works,5−7 we proposed the reaction mechanism for the reaction
of 1a and 2a (Scheme 6B). First of all, the excited photocatalyst
B was generated from A under visible-light irradiation. The key
intermediate, P-centered radical C, was generated from 2a
through SET with B and following base-promoted deprotona-
tion. Meanwhile, the oxidative addition of the C(sp2)−O bond
in tosylate 1a to a Ni0 species E gave the NiII intermediate F,
which rapidly intercepted the P-centered radical C to afford the
NiIII complex G. Further facile reductive elimination delivered
the NiI complex H and desired product 3aa via C(sp2)−P bond
formation. Lastly, both A and E were regenerated to complete
Da-Gang Yu: 0000-0001-5888-1494
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank financial support from the “973” Project from the
MOST of China (2015CB856600), the National Natural
Science Foundation of China (21502124), the “1000-Youth
Talents Plan”, and the Fundamental Research Funds for the
Central Universities. We also thank the comprehensive training
platform of the Specialized Laboratory in the College of
Chemistry at Sichuan University for compound testing.
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