A trisulfur radical anion (S3-) involved sulfur insertion reaction of 1,3-enynes: Sulfide sources control chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides

DOI: 10.1039/c9cc03604k

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Chemical Communications p. 7808 - 7811 (2019)

Update date:2022-07-29

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Authors:

Li, Jing-Hao

Huang, Qi

Rao, Weidong

Wang, Shun-Yi

Ji, Shun-Jun

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Article abstract of DOI:10.1039/c9cc03604k

Cascade cyclization reactions of S₃^-in situ generated from S₂^- with 1,3-enynes for the chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides controlled by sulfide salts are develop

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DOI: 10.1039/C9CC03604K

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•−

Trisulfur Radical Anion (S₃) Involved Sulfur Insertion Reaction of

1,3-Enynes: Sulfide Sources Control Chemoselective Synthesis of

2,3,5-trisubstituted Thiophenes and 3-thienyl Disulfides†

Received 00th January 20xx,

Accepted 00th January 20xx

Jing-Hao Li,^aQi Huang,^aWeidong Rao,^bShun-Yi Wang,*^,aand Shun-Jun Ji*^,a

DOI: 10.1039/x0xx00000x

www.rsc.org/

Cascade cyclization reactions of S₃^•−in situ generated from S^2-with trisubstituted

thiophenes

and

3-thienyl

disulfides

1,3-enynes for the chemoselective synthesis of 2,3,5-trisubstituted chemoselectively controlled by sulfide salts⁹(Scheme 1c).

thiophenes and 3-thienyl disulfides controlled by sulfide slats are

Previous work:

developed. These two protocols provide new, environment-

S₈, NaO^tBu

Ar¹

Ar²

Ar¹

Ar²

friendly and simple strategies to construct 2,3,5-trisubstituted

thiophenes and 3-Thienyl disulfides via two and six C-S bond

formations, respectively.

(a)

(b)

S₃

K₂S

S₃

Disulfides are important building blocks in organic synthesis.

They can be used as precursors of nucleophilic reagents or

radicals to participate in lots of organic synthesis reactions by

S-S bond heterolytic or homolytic cleavage.¹Thiophenes are

basic skeletons found in new electronic materials²as well as in

biologically active molecules.³And the thiophene group can be

directly introduced into the target molecule through the C-S

bond construction reaction involving dithienyl disulfide, which

is an important method for modifying the molecule in the field

of medicine and materials.

This work:

R²

Na₂S 9H₂O

R¹

R³

R²

R³

S₃

(c)

R¹

R¹, R², R³= Alkyl, Aryl

R¹

R²

R³

K₂S

R³

R²

R¹

Scheme 1 Applications of S₃^•−in thiophenes synthesis

Although S₃^•−species has been known for more than 40 years,⁴

applications of this reactive species in organic synthesis are

getting more and more attention until recent years.⁵Several

efficient methods for the synthesis of thiophenes have been

developed through the coupling annulation of reactants with

Initially, we investigated the reaction of but-1-en-3-yne-1,2,4-

triyltribenzene 1aa and K₂S 2a in DMF at 130 °C for 7 h under

atmosphere.

our

surprise,

1,2-bis(2,4,5-

triphenylthiophen-3-yl)disulfane 4aa was observed in 73%

isolated yield besides the formation of [4+1] cyclization

product 2,3,5-triphenylthiophene 3aa in 24% isolated yield

(Table 1, entry 1). Next, other sulfur reagents such as cyclo-S₈,

Na₂S·9H₂O, Na₂S₂O₃, thiourea were applied in the reaction

(Table 1, entries 2-5). It was found that different sulfur

reagents have a huge impact on the selectivity of the reaction.

When 1aa reacted with Na₂S·9H₂O under similar reaction

conditions, only 4aa was obtained in 87% isolated yield (Table

1, entry 2). The reaction of 1aa with cyclo-S₈(with NaO^tBu)

could also react smoothly to give 3aa in 35% isolated yield and

4aa in 21% isolated yield (Table 1, entry 3). There was no

reaction when Na₂S₂O₃and thiourea were applied in the

reaction (Table 1, entries 4-5).

•−

S₃in situ generated from some inorganic sulfurating

reagents.⁶Lei’s group reported an S₈and base in situ

generated S₃^•−-mediated [4+1] cyclization with 1,3-diynes for

synthesis of 2,5-diarylthiophenes (Scheme 1a).^6aMore recently,

•−

our group developed an in situ generated S₃from a K₂S-

initiated [1+2+2] cycloaddition reaction with phenylacetylenes

to afford tetra-substituted thiophenes (Scheme 1b).^6dHerein,

we describe a S₃^•−in situ generated from S^2--mediated involved

sulfur insertion reaction with 1,3-enynes^7,8to give 2,3,5-

^a.Address here.

^b.Address here.

^c.Address here.

† Footnotes relating to the title and/or authors should appear here.

Electronic Supplementary Information (ESI) available: [details of any

supplementary information available should be included here]. See

DOI: 10.1039/x0xx00000x

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J. Name., 2013, 00, 1-3 | 1

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Table 1 Sulfur reagents controlled synthesis of 3aa and 4aa^a

We examined the compatibility of various functional groups on

the aromatic ring of enynes 1aa-af, 1ba-bd, and 1ca-cc and the

View Article Online

DOI: 10.1039/C9CC03604K

results are summarized in Table 2. Gratifyingly, the optimal

conditions were compatible with a wide range of substituents,

including electron-donating groups (Me, OMe, tBu) and

electron-withdrawing groups (Cl, Br). For most of the aryl-

substituted enynes 1aa-af, 1ba-bd, and 1ca-cc, the cyclization

reaction proceeded smoothly, and the corresponding 2,3,5-

triaryl thiophenes (3aa-af, 3ba-bd, and 3ca-cc) were obtained

in good yields. It should be noted that the reaction of 3-(3,4-

DMF

Ar, 130 ^o

S reagent

1aa

3aa

4aa

yield^b(%)

entry

S reagent

K₂S

3aa

4aa

diphenylbut-3-en-1-yn-1-yl)pyridine

1ag

and

2-(1,4-

Na₂S·9H₂O

S₈+ NaO^tBu

Na₂S₂O₃

diphenylbut-1-en-3-yn-2-yl)thiophene 1be with Na₂S·9H₂O

could gave 3ag and 3be in 83% and 89% yields, respectively.

Importantly, when the substituent groups (R¹, R², R³) are alkyl

groups, the reaction could also reacted smoothly. For example,

When (4-cyclopentylbut-1-en-3-yne-1,2-diyl)dibenzene 1ah

was applied to reaction with 2a, the desired product 3ah was

observed in 82% yield.

Thiourea

^aReaction conditions: 1aa (0.3 mmol), 2 (1.2 mmol), DMF (2.0 mL), 130

^oC, under Ar, 7 h. ^bIsolated yield.

Based on the above experimental results, it was found that

Na₂S·9H₂O could be applied in the reaction to obtain 2,3,5-

trisubstituted thiophenes and K₂S could be applied in the

reaction to obtain 3-thienyl disulfides. With this promising

result in hand, we further screened the reaction conditions

(solvents, temperature and time) to optimize the two

reactions (see supporting information (SI) for more details).

Table 3 Synthesis of 3-thienyl disulfides^a,b

R¹

R³

K₂S

DMF, 130 ^o

R¹

OMe

With the established reaction conditions in hand, we explored

the substrate scope of 1,3-enynes for the two reactions. The

libraries of 2,3,5-trisubstituted thiophenes and 3-thienyl

disulfides are shown in Table 2 and Table 3, respectively.

4aa

, 73%

MeO

Table 2 Synthesis of 2,3,5- trisubstituted thiophenes^a

4ad

4ab

, 62%

, 35%

R²

R³

DMF

130 ^oC, Ar

Na₂S 9H₂O

R¹

R³

R¹

R²= R³= Ph

4cd

, 38%

R¹= C₆H₅,

, 87%

3aa

4ag

, 43%

R¹= 4-ClC₆H₄,

R¹= 4-MeC₆H₄,

, 73%

3ab

R¹

3ac

, 74%

R¹= 4- BuC₆H₄,

3ad

, 72%

3ae

3ag

3aa-af

R¹= 4-OMeC₆H₄,

, 81%

R¹= 3-MeC₆H₄,

, 78%

, 83%

3af

4ce

, 61%

Unsuccesful examples:

3ah

3be

, 82%

, 89%

R¹= R³= Ph

R²= 4-MeC₆H₄,

, 87%

3ba

4ah, trace

R²= 4-OMeC₆H₄,

, 74%

4be

, N.D.

3bb

R²= 3-BrC₆H₄,

R²= 3-MeC₆H₄,

R²

3ba-bd

3bc

, 67%

3bd

, 77%

^aStandard conditions: 1,3-enynes 1 (0.5 mmol), K₂S 2a (2.0 mmol),

3bf

, 73%

DMF (2.0 mL), at 130 °C, Ar, 5 h; Isolated yields were reported.

R¹= R²= Ph

As shown in Table 3, functional groups (Cl, OMe) on the

aromatic ring of enynes 1aa, 1ab, 1ad were well tolerated,

giving 3-thienyl disulfides 4aa, 4ab, 4ad in good isolated yields.

It should be noted that the reaction of 3-(3,4-diphenylbut-3-

en-1-yn-1-yl)pyridine 1ag with K₂S could also furnish 4ag in 43%

yields. When the substituent groups R³are alkyl groups (1cd,

1ce), the reaction could also react smoothly to give 4cd and

R³

R³= 4-MeC₆H₄,

, 74%

3ca

R³= 4-OMeC₆H₄,

, 71%

3cb

R³= 3-ClC₆H₄,

, 66%

3ca-cd

3cc

R³= CH₃,

, 31%

3cd

^aStandard conditions: 1,3-enynes 1 (0.3 mmol), Na₂S·9H₂O 2b (1.2

mmol), DMF (2.0 mL), at 130 °C, Ar, 7 h; Isolated yields were reported.

^bK₂S 2a instead of Na₂S·9H₂O 2b.

2 | J. Name., 2012, 00, 1-3

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•−

synthesis of the 3-thienyl disulfides (path b), another S₃

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reacts with intermediate A to form intermediate B’. The

4ce in 38% and 61% yields, respectively. The structure of 4cd

was further confirmed by X-ray diffraction. Unfortunately,

thiophene or cyclopentyl group substituted enynes failed to

give the desired products 4ah and 4be under the optimized

conditions.

DOI: 10.1039/C9CC03604K

intermediate B’ converts to intermediate C through S-S bond

homolysis and 1,5-hydrogen migration. The intramolecular

radical coupling of B gives intermediate 3aa’ via S-S bond

To explore the plausible mechanism of these two reactions, homolysis and releasing S₂^•−. Then, the intermediate 3aa’ is

radical-trapping experiments were performed (Scheme 2).

When 4.0 equivalent of TEMPO was added to the reaction, the

yields of 3aa and 4aa were reduced sharply. As the amount of

TEMPO was increased to 5.0 equivalents and 6.0 equivalents

respectively, these two reactions were almost fully

suppressed. This observation indicated that a radical pathway

might be involved in the reactions.

oxidized to form the disulfide product 4aa.

-S₂

3aa

Na₂S/K₂S + DMF

S₃

Path a

1,3- migration

S₃

S₃Ph

S₃

Reaction I

1aa

Path b

TEMPO (4 equiv)

DMF, 130 ^o

-S₂

1,5-H migration

Na₂S 9H₂O

1aa

3aa

, 4 equiv

, 26%

-S₂

TEMPO (5 equiv)

Na₂S 9H₂O

DMF, 130 ^o

4aa

3aa'

1aa

3aa

, 4 equiv

, trace

Reaction II

Scheme 4 A plausible mechanism.

TEMPO (4 equiv)

DMF, 130 ^o

K₂S

In summary, we have developed S₃^•−in situ generated from S^2-

mediated cascade cyclization reactions with 1,3-enynes for the

chemoselective synthesis of 2,3,5-trisubstituted thiophenes

and 3-Thienyl disulfides controlled by sulphide salsts. These two

protocols provides new, environment-friendly and simple

strategies to construct 2,3,5-trisubstituted thiophenes and 3-thienyl

disulfides via two and six C-S bond formations under transition

metal-free conditions, respectively.

3aa

4aa

, 38%

1aa

, 15%

, 4 equiv

TEMPO (6 equiv)

DMF, 130 ^o

K₂S

1aa

, 4 equiv

3aa

4aa

, <10%

, trace

Scheme 2 Radical-trapping experiments.

To gain in-depth insight into the mechanism for the synthesis

of 3-thienyl disulfides, some control experiments were carried

We gratefully acknowledge the National Natural Science

Foundation of China (21772137, 21542015 and 21672157),

PAPD, the project of scientific and technologic infrastructure of

Suzhou (SZS201708), the Major Basic Research Project of the

Natural Science Foundation of the Jiangsu Higher Education

Institutions (No.16KJA150002), and Soochow University for

financial support. We thank Fei Wang in this group for

reproducing the results of 3ae, 3ag, 3ba, 3be, 3bf, and 4ce.

out

(Scheme

3).

First,

product

5-methyl-2,4-

diphenylthiophene-3-thiol 3cd’ could be obtained in 15%

isolated yield after pent-3-en-1-yne-1,3-diyldibenzene 1cd

reacted with K₂S under the standard condition for 1 hour. Then,

1,2-bis(5-methyl-2,4-diphenylthiophen-3-yl)disulfane 4cd was

obtained successfully after 3cd’ was put in DMF at 130 C for

another 4 hours. These results indicate that the thiophene-3-

thiol might be an intermediate in reaction for the synthesis of

3-thienyl disulfides.

Conflicts of interest

There are no conflicts to declare.

, 15%

1 h

4 h

K₂S

DMF, 130 ^o

4cd

3cd'

, 53%

1cd

Notes and references

Scheme 3 Control experiments.

^aKey Laboratory of Organic Synthesis of Jiangsu Province, College

of Chemistry, Chemical Engineering and Materials Science &

Collaborative Innovation Center of Suzhou Nano Science and

Technology, Soochow University, Suzhou, 215123, P. R. China;

Based on the reported literatures^5b,6and our experimental

results (the deuterated experimental results could be seen in

SI for more details), two reaction mechanisms were proposed

•−

in Scheme 4.¹⁰First, S₃in situ generated from K₂S or Na₂S

attacks the but-1-en-3-yne-1,2,4-triyltribenzene 1aa to ^bJiangsu Key Laboratory of Biomass-based Green Fuels and

generate the radical anion intermediate A. In the generation of Chemicals, College of Chemical Engineering, Nanjing Forestry

the 2,3,5-trisubstituted thiophenes (path a), the intermediate University, Nanjing 210037, China.

A converts to intermediate B by 1,3-hydrogen migration. The

Fax:+86-512-65880307; Tel:+86-512-65880307; E-mail: shunyi

intramolecular radical coupling of B gives the cyclization

@suda.edu.cn.; shunjun@suda.edu.cn.

product 3aa via S-S bond homolysis and releasing S₂^•−. For the

J. Name., 2013, 00, 1-3 | 3

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†Electronic Supplementary Information (ESI) available: [details

of any supplementary information available should be included

here]. See DOI: 10.1039/x0xx00000x/

View Article Online

DOI: 10.1039/C9CC03604K

The syntheses and characterization of compounds 3ae, 3ag, 3ba,

3be, 3bf and 4ce were repeated and checked by Fei Wang in our

group.

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10 The reaction mechanism of Na₂S·9H₂O involved in the

synthesis of thiophenes is very complicated, and we illustrate

a possible mechanism here.

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Article Doi

A trisulfur radical anion (S3-) involved sulfur insertion reaction of 1,3-enynes: Sulfide sources control chemoselective synthesis of 2,3,5-trisubstituted thiophenes and 3-thienyl disulfides

DOI: 10.1039/c9cc03604k

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