Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

Article abstract of DOI:10.1039/d1cc00769f

We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).

Full text of DOI:10.1039/d1cc00769f

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Palladium-catalyzed one-pot phosphorylation of
phenols mediated by sulfuryl fluoride†
Cite this: Chem. Commun., 2021,
57, 4588
Yiyuan Zhang,‡abcd Wanting Chen,‡abcd Tingting Tan,abcd Yuang Gu,abcd
Shuning Zhang,abcd Jie Li,a Yan Wang,abcd Wei Hou,e Guang Yang,a Peixiang Ma*a
Received 9th February 2021,
Accepted 29th March 2021
a
and Hongtao Xu
*
DOI: 10.1039/d1cc00769f
rsc.li/chemcomm
We report a general palladium-catalyzed one-pot procedure for the transition metal-catalyzed reactions, such as Suzuki reaction,6a,7b,11
synthesis of phosphonates, phosphinates and phosphine oxides Buchwald amination,6a,7b,12 Sonogashira reaction,6a,7b Catellani
from phenols mediated by sulfuryl fluoride. It features mild conditions, reaction,13 and nickel-catalyzed carboxylation.14 As we are embark-
broad substrate scope, high functionality tolerance and water insensi- ing on the building of a natural product-based DEL (nDEL),15 we
tivity. The utility of this procedure has been well demonstrated by gram- have developed the on-DNA palladium-catalyzed Suzuki, Buchwald
scale synthesis, sequential synthesis of click chemistry building blocks, and Sonogashira reactions of ArOSO2F for the on-DNA decoration of
late-stage decoration of drugs and natural products and on-DNA natural products.6a
synthesis of phosphine oxide for a DNA-encoded library (DEL).
On the other hand, organophosphorus compounds are well
investigated compounds that play a key role in chemistry,
Since the pioneering work of the Sharpless group, sulfur(VI) biology and medicine. Among them, phosphonates, phosphinates
fluoride exchange (SuFEx),1 deriving from ‘‘old-school chemistry’’, and phosphine oxides are emerging pharmacophores.16 As
has gained emerging applications in organic chemistry,2 material uncharged highly polar functionalities, they can not only offer
science,3 medicinal chemistry,4 chemical biology,5 and DNA- the unique feature of a strong hydrogen-bond acceptor installed
encoded libraries (DELs).6 Among various SuFEx entities, aryl on the centre of a tetrahedron with three potential derivatization
fluorosulfates (ArOSO2F) have attracted significant attention due anchors, but also can help to increase the water solubility and
to their unique stability and reactivity. They are readily available metabolic stability. In addition, the incorporation of phosphorus
from the reaction of phenols with gaseous sulfuryl fluoride into the fragments of the designing hit library will be greatly
(SO2F2) or the solid reagents fluorosulfuryl imidazolium salt beneficial to the 31P NMR-based hit screening campaign.17 Thus,
and [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF).7 numerous efforts have been spearheaded toward the synthesis of
Under appropriate conditions, the reaction can exclusively take organophosphorus. Apart from the traditional organolithium,
place at the sulfur, for example, typical SuFEx of amines with Grignard protocols and Michaelis–Arbuzov reaction, palladium-
–OSO2F could generate aryl sulfamates,8 and the ultrafast catalyzed C–P bond formation pioneered by Hirao represents the
18F–19F isotopic exchange of ArOSO2F could deliver 18F PET most straightforward method.18 So far, many efficient protocols
tracer.9 –OSO2F can also act as a good leaving group, for instance, have been reported, such as transition metal (Pd,19 Ni,20 and
the SO2F2 mediated nucleophilic substitution of aliphatic alcohols.10 Cu21)-catalyzed synthesis, photosensitizer-catalyzed synthesis,22
Significantly, they have been used as versatile electrophiles in photosensitizer-free visible light-catalyzed synthesis.23 photo-
induced transition metal-free synthesis,24 and photoinduced
a Shanghai Institute for Advanced Immunochemical Studies, ShanghaiTech
University, Shanghai, 201210, China. E-mail: xuht@shanghaitech.edu.cn,
mapx@shanghaitech.edu.cn
transition metal dual-catalyzed synthesis.25 These reactions
generally use aryl halides,20a aryl triflates,20c,25a tosylates,19b
mesylates,19b and diaryliodonium salts,21b etc. as electrophiles.
However, many of them suffer from relatively harsh conditions
such as high temperature (4100 1C),19a,b,d,e,21a,26 and the use of
a strong base (tBuOK, tBuONa, etc.),23,24 which hinders the
diverse synthesis of organophosphorus greatly.
Taking the above observations into account, we envisioned
the synthesis of organophosphorus by using ArOSO2F as an electro-
phile. Such a protocol may have multiple benefits, (1) ArOSO2F are
phenol-derived electrophiles, which, as compared to aryl halides,
b School of Life Science and Technology, ShanghaiTech University, Shanghai,
201210, China
c Institute of Biochemistry and Cell Biology, Shanghai Institutes for Biological
Sciences, Chinese Academy of Sciences, Shanghai, 200031, China
d University of Chinese Academy of Sciences, Beijing, 100049, China
e College of Pharmaceutical Science, and Institute of Drug Development & Chemical
Biology, Zhejiang University of Technology, Hangzhou, 310014, China
† Electronic supplementary information (ESI) available: Experimental proce-
dures, and characterization data. See DOI: 10.1039/d1cc00769f
‡ These authors contributed equally.
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can be used as a more sustainable starting material as most phenols
are readily available from natural biodegradation of biomass in an
environment-friendly way. (2) Reactions with ArOSO2F as an
electrophile would offer new synthetic strategies for late-stage
phosphorylation of phenol bearing drugs and natural products.
(3) Compared with triflic anhydride, the reaction of SO2F2 in the
presence of a weak base can discriminate phenolic hydroxyl and
aliphatic hydroxyl, and hence may help to shorten the synthesis.
(4) ArOSO2F can be readily synthesized by reaction of phenols
with gaseous SO2F2 in excellent quantitative yields. Thus, the
reaction may have great potential for the convenient one-pot
sequential synthesis. Herein we report mild palladium-catalyzed
phosphorylation of aryl- or heteroaryl phenols, providing phos-
phonates, phosphinates and phosphine oxides in a one-pot
procedure mediated by sulfuryl fluoride (Fig. 1c).
To test our hypothesis, ArOSO2F 1a and diethyl phosphite 2a
were chosen as the model substrates for the preliminary optimi-
zation of the reaction conditions (Table S1, ESI†). Initially, the
screening of the palladium source and ligands indicated that the
reaction could take place readily to produce 3a (95%) by a
catalytic system of Pd(OAc)2 (10%) and dppf (20%) in acetonitrile
at 80 1C (entry 9). Reducing the loading of Pd(OAc)2 (5% and 2%)
and dppf (10% and 4%) has no significant influence on the yield
of 3a (entry 1 and 10). It should be noted that dppf was the most
potent ligand, a sharply decreased yield of 3a was detected in
the absence of dppf (entries 3–7). Inorganic base (Na2CO3) and
air showed a detrimental effect on this conversion (entries 11
Scheme 1 Substrate scope investigation. One-pot synthesis: (i) 1s (1
equiv.), SO2F2 (bolloom), Et3N (2 equiv.), 3 h; (ii) TMSOH (3 equiv.), 30
min; (iii) standard conditions. aYield of standard conditions; byield of one-
pot synthesis.
and 19). Besides, lower yields were achieved when using and aryl H-phosphinates) compounds (Scheme 1). To our delight,
N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) this reaction is amenable when alkyl (3b), alkoxy (3c, 3h and 3l),
or 1,4-dioxane as solvents (entries 15–17). Delightfully, a comparable halogen (3e, 3f and 3i), carboxyl (3g), carboxylic ester (3s), cyano
yield of 93% was obtained in the presence of 20% water (entry 14), (3j and 3m), and heterocycle (3p–3s) were incorporated, providing
highlighting its potential for on-DNA phosphorylation of phenols, as the expected phosphonates in good to excellent yields. Generally,
on-DNA reactions are typically executed in the presence of water.27 both electron-donating (3a–3c, 3h and 3l) and -withdrawing
When nickel was employed as the catalyst, as was independently groups (3d, 3g, 3j, 3k and 3m) were tolerated. Notably, this
reported by Ding,28 the reaction also proceeded efficiently, albeit reaction discriminates bromide and chloride well to generate
under slightly higher temperature.
the corresponding chloride and bromide substituted phospho-
With the optimal conditions in hand, we next focused on nates in excellent yields (3e, 3f and 3i), thus providing additional
evaluating the generality of the reaction by using a series of aryl anchors for further diversification. Although the sterical hindrance
fluorosulfates and P(O)H (phosphites, secondary phosphines at the ortho-position would reduce the yields, ortho-di-tert-butyl-
phenyl fluorosulfate 3n and 2,6-dimethylphenyl fluorosulfate 3o
still delivered the expected phosphonates in acceptable yields.
Moreover, other phosphites were also compatible with the
established conditions delivering the corresponding phospho-
nates in good to excellent yield (3aa–3ad), except for dibenzyl
phosphite 2ae, which delivered 3ae in moderate yield (52%).
This may be attributed to the instability of the benzyl moiety of
2ae during the reaction.29 As presented in Scheme 1, both of the
secondary phosphines oxides and aryl H-phosphinates reacted
smoothly, delivering phosphinate 3af and tertiary phosphine
oxides (3ag–3ai) in excellent yields, thus further highlighting the
generality of the established conditions. It is also worth noting
that the reaction of 1b with optically pure ((RP)-(À))-menthyl
benzylphosphinate could deliver enantiomerically pure P-chiral
3aj with retention of the configuration at the phosphorus atom.
To save the additional isolation step needed for the conversion
Fig. 1 Organophosphorus containing drugs and the synthesis of phosphates. of phenol to ArOSO2F, we next evaluated the feasibility of one-pot
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synthesis of ArOSO2F from phenols directly. Initially, the reaction
of 1as with SO2F2 in the presence of N,N-diisopropylethylamine for
3 h provided 1a in nearly quantitative yield. Without further
purification, 1a was reacted with 2a under the standard conditions;
however, the desired aryl phosphonate 3a was only produced
(31%) along with two major side products 4 and 5 (Scheme 2a).
The production of the side products probably can be attributed to
the fluoride ions generated during the synthesis of ArOSO2F.30 It is
conceived that the fluoride ion can react with trimethylsilanol
(TMSOH) to generate the highly volatile trimethylfluorosilane
(TMSF, boiling point,16 1C at 1 atm), which can be easily dislodged
from the reaction system by simply purging with argon.4b Inter-
estingly, following the TMSOH procedure, the one-pot synthesis
could deliver 3a with a comparable yield (90%). The investigation
of the substrate scope showed that the one-pot procedure has
broad substrate scope, and high functional group tolerance just
like the stepwise synthesis (Schemes 1 and 3). Moreover, gram
scale one-pot phosphorylation of 1as could produce 3a in 86%
yield, highlighting the practical utility of this procedure. The
convenience of the reaction was further demonstrated by a
sequential synthesis of a click chemistry synthon 6. Significantly,
on-DNA phosphorylation of D1 with phosphines could deliver D2
in satisfactory yield by slightly modifying the standard conditions
(Scheme 2d).
Scheme 3 Late-stage modification of drugs and natural products. aYield
of stepwise synthesis. bYield of one-pot synthesis.
discriminate phenolic and aliphatic hydroxyl in 1us highlighted
further the superiority of SO2F2 over triflates (Scheme 3b). These
results not only further demonstrated the high functionality (free
hydroxyl, keto and amido) tolerance of this methodology, but also
showed its great potential in the late-stage functionalization of
bioactive molecules.
To further demonstrate the utility of this method, we sought
to investigate whether the methodology could be used for the
late-stage decoration of phenol containing complex molecules
such as natural product 1t, approved drug 1u and bioactive
intermediate 1v. As shown in Scheme 3, under the established
standard conditions or one-pot procedure, we were pleased to
obtain the expected phosphonates 3t, 3u, and 3v in high to
excellent yields. The no reactivity on the third phenol functionality
of 1ts is probably due to the hydrogen bond effect of the phenol
with the carboxyl group (Scheme 3a). The ability of SO2F2 to
In summary, we have developed a general palladium-catalyzed
phosphorylation of aryl fluorosulfates. This reaction features mild
conditions, broad substrate scope and water tolerance. Notably,
the tolerance of Ar–Br and Ar–Cl offers opportunities for diversity
synthesis by orthogonal couplings. Significantly, we demonstrated
the convenience of this reaction by one-pot synthesis of aryl
phosphonates, aryl phosphinates and phosphine oxides from
phenols without the erosion of the yields. The utilization of the
reaction has been well demonstrated by one-pot gram-scale synth-
esis, sequential synthesis of modular click chemistry building
blocks, late-stage decoration of drugs and natural products, and
on-DNA synthesis. Overall, such a method can be used as a
powerful tool for the synthesis of aryl phosphonates, phosphinates
and phosphine oxides from aryl fluorosulfates or phenols, and will
further enrich the late-stage functionalization (LSF) toolbox of
natural products and/or other bioactive molecules and DNA-
encoded libraries.
This work was partially supported by the National Nature
Science Foundation of China (No.: 21977070, 21907085, U19A2011).
Conflicts of interest
There are no conflicts to declare.
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