Ni nanoparticle-confined covalent organic polymer directed diaryl-selenides synthesis

Article abstract of DOI:10.1039/d0dt01327g

The present work describes the preparation of a new covalent organic polymer (COP) and its application as a hetero support for diaryl selenides synthesis. A nitrogen rich COP (CGP) has been synthesized via SNAr reaction of cyanuric chloride with guanidinium hydrochloride. The successful confinement of COP with Ni nanoparticles through post-synthetic transformations (Ni?CGP) provides excellent catalytic activity for the transformation of aryl halides into diaryl selenides using elemental selenium powder. The synthetic transformations are well confirmed using various modern analytical and spectroscopic techniques which reveal high chemical and thermal durability. The N-rich framework of CGP fortifies the confinement of Ni NPs. Ni?CGP provides an efficient approach for diaryl selenides synthesis using a very cheap selenating reagent under water benign solvent conditions (DMSO?:?H2O) at room temperature with high reusability. Significantly, our work not only contributes the opportunity for developing economical and effective non-noble metal decorated COPs as heterogeneous catalysts, but also delivers an efficient approach to produce industrially important C-Se coupling products.

Full text of DOI:10.1039/d0dt01327g

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Dixit, S. Raghothama and S. K. Awasthi, Dalton Trans., 2020, DOI: 10.1039/D0DT01327G.
Volume 46
Number 10
14 March 2017
Pages 3073-3412
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Royal Society of Chemistry peer review process and has been
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ISSN 0306-0012
COMMUNICATION
Douglas W. Stephen et al.
shall the Royal Society of Chemistry be held responsible for any errors
N-Heterocyclic carbene stabilized parent sulfenyl, selenenyl,
and tellurenyl cations (XH+, X = S, Se, Te)
or omissions in this Accepted Manuscript or any consequences arising
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&'()*( +, -,. )+/0*. 1)234-*

&'()*( +, -,. )+/0*. 1)234-*
Dalton Transactions
Page 7 of 8
View Article Online
DOI: 10.1039/D0DT01327G
;$5&"#) #1*
A67489:
Ob7
OK7
>7XR7 F4-3P N7 U),P v7 d)-3P R7 t:)-3P d7XU7 >,-3P #7XR7 >0
)-+ d7 d)-3P N= A$= !"#$= B)&=P OIHHP EGGP HKbH`XHKbOO7
@)A S7 #:)0+:)2<P >0;,+:P S7 &2)Q)*:P W7 S7 [,3:) )-+ F7
!7 [)*2)1P A- ,= N= !"#$=P OIOIP EGP ^b`KX^bbHu @;A U7
S01)2P W7 S7 [,3:)P [7 S01)2P >0;,+: )-+ F7 !7
[)*2)1P / '.)1 Q- 13=P OIOIP ISP HK`JXHKa^u @5A >0;,+:P
S7 #:)0+:)2<P S7 &2)Q)*: )-+ F7 !7 [)*2)1P A00'= BD-2=
B&%=P OIOIP J=SP H^^KIOu @+A >0;,+:P W7 S7 [,3:)P S7
#:)0+:)2<P U7 S01)2 )-+ F7 !7 [)*2)1P A!B T$#* P
OIHbP GP H`JaaXH`Jb_7
JI7
JH7
@)A 87X$7 #),P 87X]7 80)-3P t7 #:(-P ]7 S)2)+(-4VP N7 $x )-+
7 #),P A!B A00'= J .#-= ;1.#-2 &#3P OIHaP SP _OJHX_OJ`u
@;A U7XN7 #:(-P j7X]7 $4P #7X#7 t:),P 87X#7 [)P N7X$7 S)-P R7X]7
j4-P #7Xj7 #:(- )-+ R7X]7 F,-3P ;1)-*= !"#$=P OIHbP JUP
O`abXO`b_u @5A %7 &)2QP N7 N)5QP R7 80P >7 d)-P >7 80)-3P R7
N4-P &7X#7 [)-(**P >7 R)V+4P t7 (- )-+ d7 t:)-3P
I 1)3& '#P OIOIP E<P O_K`XO`IO7
87 A7 &).('P i7 S)2)+)*P A7 #)-'4(2P N7 &)2QP %7 F(-4VP R7 N0-3P
[7 A.4':)- )-+ #7 !7 R)B0VP N= J .#-= !"#$=P OIHOP <<P
b^JHXb^Ja7
JO7
JJ7
&7 &0.:4)2)/P >7X[7 #:,P R7X 7 $(( )-+ d7X>7 A:-P N= J .#-=
!"#$= AP OIH_P GP `aKOX`aKa7
&7 ]:)-/)P >7 S7 F)*P S7 ]:0-4)P F7 &2)+:)-P !7 8)<)*:4P R7
84/4Q).)P >7 "2'( )-+ A7 ]:)014QP A!B BD3. %1 ,'# !"#$=
>1*=P OIHbP PP OIOXOIK7
J^7
J_7
J`7
Ja7
Jb7
JK7
j7 d0P ]7 d)-3P t7 R)-3 )-+ $7 #:(-P N= J .#-= !"#$= AP
OIHKP UP _`_IX_`__7
[7 U0V('P !7 >,3)-54P 7 A<2)-54 )-+ [7 AQP P"+3= !"#$=
!"#$= P"+3=P OIH`P ETP OH`_KXOH``a7
>7X&7 $((P W7 [('',-P A7 [7 >:)2466 )-+ N7X[7 $(B(Z0(P I#R
N= !"#$=P OIHbP I<P H_^bbXH_^K`7
R7 i0P d7 R0P d7 t:)-3P v7 80)-3P N7 R)-P #7 &)- )-+ U7 R0P
P)'+$= !"#$=P OIHbP SP ^HO_X^HJH7
R7 i)-3P N7 [4),P j7 R)-3P R7 t:0 )-+ U7 d)-3P !"#$= >1*=
N=P OIOIP GTJP HOJbJI7
R7 N4)-3P "7 G:P >7 87 N,,P G7 ]0<0Q5)Q42P j7 #:(-P >7 87 $((P
[7 80)-3P d7 S7 >(,-3P N7 87 S41P N7Xp7 ,:+(P >7 S7 S9)QP
N7Xd7 R,, )-+ 7 >7 0,66P A!B I 1)P OIHKP EGP _O_HX_O_b7
@)A $7 ]4P F7 [(-3P v7 ]0P R7 $4-P F7 d)-3 )-+ !7 j4(P P"+3=
!"#$= !"#$= P"+3=P OIH`P ETP JH_J^XJH_^Hu @;A &7 &24(.,P
c7 W4*.,2P S7 W,0-(:P [7 G<)1)P [7 A;+X$(6+4' )-+ 7
Fy)VP A00'= BD-2= B&%=P OIHOP <JTP bbIaXbbHJ7
^I7
^H7
^O7
^J7
^^7
^_7
^`7
R7 87 "Q0:)2)P 87 [,24P !7 >)4., )-+ R7 "9)1,.,P N= A$=
!#- $= B)&=P OIIaP S=P _^`X__O7
$7 d)-3P j7 $40P [7 R)-3P R7 i)- )-+ N7 t:)-P >D-= N= ;1)-*=
!"#$=P OIIKP <==SP bKaXKIO7
"7 &7 ]('(.*Q)<) )-+ c7 &7 A-)-4Q,BP !"#$= K#6=P OIHHP EEEP
H_K`XH`J`7
R7 N4)-3P R7 v4-P >7 j4(P j7 t:)-3P N7 F,-3 )-+ F7 [)P T-*=
S#..=P OIIKP EEP _O_IX_O_J7
R7 $4P #7 W4(P 87 d)-3P j7 $4P i7 c(2?,,2. )-+ #7 F0)-P >D-= N=
T-*= !"#$=P OIHHP GPP aJJHXaJJb7
W7 !)-4305:4P B+1'#..P OII_P EEP H`baXH`KI7
!:4* /,02-)' 4* f !:( ,<)' >,54(.< ,6 #:(14*.2< OIMM
N= I $#7P OIHJP ==P HXJ e U
&'()*( +, -,. )+/0*. 1)234-*

Dalton Transactions
Page 8 of 8
View Article Online
DOI: 10.1039/D0DT01327G
Graphical Abstract
Acetone, Δ
TEA
+
1
2
aq. NaBH4
NiCl2
R
Se
Se
+
R
R
X = Br, I
X