Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

Article abstract of DOI:10.1039/c6cc07846j

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O₂ (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Full text of DOI:10.1039/c6cc07846j

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Yatabe, J. Hasegawa, K. Yamaguchi and N. Mizuno, Chem. Commun., 2016, DOI: 10.1039/C6CC07846J.
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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
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DOI: 10.1039/C6CC07846J
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ꢃ]((Œꢀꢂš]}v ~ów5• ꢀvꢀoÇ•]• ŒꢁÀꢁꢀoꢁꢃ šZꢀš šZꢁ ha{rî •µ‰‰}Œš ~Ç9ath• Á]šZ Œꢁ•‰ꢁꢂš š} íꢀ ꢁÀꢁv µvꢃꢁŒ ꢀv ꢀ]Œ ꢀšu}•‰ZꢁŒꢁU
PŒꢀꢃµꢀooÇ ꢂZꢀvPꢁꢃ š} avïhð ꢀ• šZꢁ Œꢁµ•ꢁ ꢁƉꢁŒ]uꢁvš Áꢀ• ꢀvꢃ šZꢁ Ç]ꢁoꢃ }( îꢀ ]vꢂŒꢁꢀ•ꢁꢃ (Œ}u ïí9 š} ðì9 ~Çꢀꢄoꢁ {ðU
Œꢁ‰ꢁꢀšꢁꢃ ~C]PX {ïU 9{L••Xíó ÇZ]• ]• o]lꢁoÇ ꢃµꢁ š} šZꢁ Œꢁꢃµꢂš]}v }( ꢁvšŒÇ í À•X ꢁvšŒÇ îU 9{L••X ÇZꢁŒꢁ(}ŒꢁU Ç9ath ]• šZꢁ ꢄꢁššꢁŒ
uꢀvPꢀvꢁ•ꢁ •‰ꢁꢂ]ꢁ• ꢀvꢃ šZꢁ ꢁo]u]vꢀš]}v }( šZꢁ šµvvꢁo Y= }Æ]ꢃꢀvš šZꢀv hî (}Œ šZꢁ !µl!oîhïrꢂꢀšꢀoÇÌꢁꢃ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}vX
•‰ꢁꢂ]ꢁ• ]v šZꢁ ha{rî •µ‰‰}ŒšXíó Lv ꢀꢃꢃ]š]}vU šZꢁ šŒꢀv•u]••]}v íZꢁv šZꢁ !µl!oîhïrꢂꢀšꢀoÇÌꢁꢃ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}v Áꢀ• ꢂꢀŒŒ]ꢁꢃ
ꢁoꢁꢂšŒ}v u]ꢂŒ}•ꢂ}‰Ç ~Ç9a• ꢀvꢀoÇ•]• ꢁÆZ]ꢄ]šꢁꢃ šZꢀš šZꢁ ꢀÀꢁŒꢀPꢁ }µš µ•]vP Ç9ath ꢀ• šZꢁ }Æ]ꢃꢀvš µvꢃꢁŒ ꢀv !Œ ꢀšu}•‰ZꢁŒꢁU îꢀ
‰ꢀŒš]ꢂoꢁ •]Ìꢁ }( !µ ]vꢂŒꢁꢀ•ꢁꢃ (Œ}u ïXõ vu ~(Œꢁ•Z ꢂꢀšꢀoÇ•š• š} Áꢀ• }ꢄšꢀ]vꢁꢃ ]v ïï9 Ç]ꢁoꢃ ~Çꢀꢄoꢁ {ðU ꢁvšŒÇ ðU 9{L••X Lv šZ]• ꢂꢀ•ꢁU
î n WX bꢀuꢁXU îìíîU ììU írï
ÇZ]• i}µŒvꢀo ]• ž ÇZꢁ w}Çꢀo {}ꢂ]ꢁšÇ }( /Zꢁu]•šŒÇ îìÆÆ
toꢁꢀ•ꢁ ꢃ} v}š ꢀꢃiµ•š uꢀŒP]v•

toꢁꢀ•ꢁ ꢃ} v}š ꢀꢃiµ•š uꢀŒP]v•
ChemComm
Page 3 of 4
View Article Online
DOI: 10.1039/C6CC07846J
W}µŒvꢀo bꢀuꢁ
/haaÜbL/!ÇLhb
Çꢀꢄoꢁ í {ꢂ}‰ꢁ }( šZꢁ !µlha{rîrꢂꢀšꢀoÇÌꢁꢃ }Æ]ꢃꢀš]Àꢁ rUtrꢃꢁZÇꢃŒ}Pꢁvꢀš]}vꢀ
•š}]ꢂZ]}uꢁšŒÇ ]vꢃ]ꢂꢀšꢁ• šZꢀš Ç9ath ꢂꢀv Á}Œl ꢀ• ꢀ }vꢁr
ꢁoꢁꢂšŒ}v }Æ]ꢃꢀvš (}Œ šZꢁ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}vX a}Œꢁ}ÀꢁŒU šZꢁ
ꢂ}všŒ}o ꢁƉꢁŒ]uꢁvš •Z}Áꢁꢃ šZꢀš Ç9ath ]š•ꢁo( ꢂ}µoꢃ v}š
‰Œ}u}šꢁ šZꢁ Œꢁꢀꢂš]}v ~Çꢀꢄoꢁ {ðU ꢁvšŒÇ ôU 9{L••X Lš Zꢀ• ꢄꢁꢁv
Œꢁ‰}Œšꢁꢃ šZꢀš Ç9ath ꢂꢀv ꢀꢂš ꢀ• ꢀ }vꢁrꢁoꢁꢂšŒ}v }Æ]ꢃꢀvš š}
ꢀꢄ•šŒꢀꢂš ꢀ ZÇꢃŒ}Pꢁv ꢀš}u (Œ}u !µtI •‰ꢁꢂ]ꢁ• ꢀvꢃ šZꢁv Ç9ath
]š•ꢁo( ]• ꢂ}vÀꢁŒšꢁꢃ ]vš} Ç9athIXîí ÇZꢁŒꢁ(}ŒꢁU !µtI •‰ꢁꢂ]ꢁ• ]•
o]lꢁoÇ (}Œuꢁꢃ ꢃµŒ]vP šZꢁ ‰Œꢁ•ꢁvš }Æ]ꢃꢀš]Àꢁ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}v
ꢀvꢃ šZꢀš šZꢁ }Æ]ꢃꢀš]}v }( šZꢁ !µtI •‰ꢁꢂ]ꢁ• š} ŒꢁPꢁvꢁŒꢀšꢁ
ꢀꢂš]Àꢁ !µ •‰ꢁꢂ]ꢁ•îî ]• ]vꢂoµꢃꢁꢃ ]v šZꢁ ꢂꢀšꢀoÇš]ꢂ ꢂÇꢂoꢁX ÇZꢁ ꢀꢄ}Àꢁr
uꢁvš]}vꢁꢃ ‰Œ}u}š]}vꢀo ꢁ((ꢁꢂš• }( Ç9ath •µPPꢁ•š šZꢀš šZꢁ
}Æ]ꢃꢀš]}v }( šZꢁ !µtI •‰ꢁꢂ]ꢁ• ꢄÇ hî ]• o]lꢁoÇ ŒꢀšꢁrꢃꢁšꢁŒu]v]vP
Entry
Substrate
Product
Temp Time Conv. Yield
(°C)
(h)
(%)
(%)
O
O
1
50
8
94
90
1a
1b
2a
N
O
N
O
O
N
2b
2b'
86 86(78i)
+
4 : 1i
O
2
50
70
80
16
24
8
N
O
N
98 70j(64)
•šꢁ‰ (}Œ šZꢁ !µl!oîhïrꢂꢀšꢀoÇÌꢁꢃ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}v }( íꢀ
X
3
1c
1d
2c
2d
bꢁÆšU šZꢁ }Æ]ꢃꢀš]Àꢁ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}v }( íꢀ Áꢀ• ꢂꢀŒŒ]ꢁꢃ }µš
]v šZꢁ ‰Œꢁ•ꢁvꢂꢁ }( ^!µlha{rî_X Ç} }µŒ •µŒ‰Œ]•ꢁU ꢁÀꢁv µvꢃꢁŒ ꢀv
!Œ ꢀšu}•‰ZꢁŒꢁU îꢀ Áꢀ• •š]oo ‰Œ}ꢃµꢂꢁꢃ ]v õí9 ~Çꢀꢄoꢁ {ðU ꢁvšŒÇ óU
9{L••X ÇZ]• Œꢁ•µoš ]• ]v •ZꢀŒ‰ ꢂ}všŒꢀ•š š} šZꢁ ꢀꢄ}Àꢁruꢁvš]}vꢁꢃ
Œꢁ•µoš µ•]vP !µl!oîhïV îꢀ Áꢀ• ZꢀŒꢃoÇ }ꢄšꢀ]vꢁꢃ µvꢃꢁŒ ꢀv !Œ
ꢀšu}•‰ZꢁŒꢁ ÁZꢁv µ•]vP !µl!oîhï ~Çꢀꢄoꢁ {ðU ꢁvšŒÇ ïU 9{L••X Lš
Áꢀ• ꢂ}v(]Œuꢁꢃ ꢄÇ šZꢁ ów5 ꢀvꢀoÇ•]• šZꢀš šZꢁ ha{rî •µ‰‰}Œš
ꢂ}u‰oꢁšꢁoÇ Œꢁꢃµꢂꢁꢃ š} avïhð ꢀ(šꢁŒ šZꢁ Œꢁꢀꢂš]}v }( íꢀ µvꢃꢁŒ ꢀv
!Œ ꢀšu}•‰ZꢁŒꢁ ~C]PX {òU ꢂU 9{L••X Lv ꢂ}všŒꢀ•šU šZꢁ •šŒµꢂšµŒꢁ }(
ha{rî Œꢁuꢀ]vꢁꢃ ꢀou}•š µvꢂZꢀvPꢁꢃ ÁZꢁv šZꢁ •ꢀuꢁ Œꢁꢀꢂš]}v
Áꢀ• ‰ꢁŒ(}Œuꢁꢃ µvꢃꢁŒ ꢀv ꢀ]Œ ꢀšu}•‰ZꢁŒꢁ ~C]PX {òU ꢄU 9{L••X
ÇZꢁ•ꢁ Œꢁ•µoš• •µPPꢁ•š šZꢀš ha{rî ꢂꢀv ꢀꢂš ꢀ• šZꢁ }Æ]ꢃꢀvš š}
‰Œ}u}šꢁ šZꢁ }Æ]ꢃꢀš]}v }( šZꢁ !µtI •‰ꢁꢂ]ꢁ• š} ŒꢁPꢁvꢁŒꢀšꢁ
ꢀꢂš]Àꢁ !µ •‰ꢁꢂ]ꢁ•îî ꢀvꢃ šZꢀš šZꢁ Œꢁꢃµꢂꢁꢃ ha{rî ꢂꢀv ꢄꢁ
Œꢁ}Æ]ꢃ]Ìꢁꢃ ꢄÇ hî ~]v ꢀ]Œ•Xíò I}ÁꢁÀꢁŒU ]š ]• o]lꢁoÇ šZꢀš šZꢁ
Œꢁ}Æ]ꢃꢀ]š}v }( ha{rî ꢄÇ hî ]• •}uꢁÁZꢀš •o}ÁꢁŒ šZꢀv šZꢁ
}Æ]ꢃꢀš]}v }( šZꢁ !µtI •‰ꢁꢂ]ꢁ• ꢄÇ ha{rîV ZꢁvꢂꢁU ha{rî Áꢀ•
PŒꢀꢃµꢀooÇ Œꢁꢃµꢂꢁꢃ š} avïhð ]v šZꢁ ꢀꢄ}Àꢁruꢁvš]}vꢁꢃ Œꢁ‰ꢁꢀšꢁꢃ
Œꢁµ•ꢁ ꢁƉꢁŒ]uꢁvš• ~C]PX {ïU 9{L••Xíó CµŒšZꢁŒu}ŒꢁU Ç9ath ꢃ]ꢃ
v}š ꢀꢂꢂꢁoꢁŒꢀšꢁ šZꢁ }Æ]ꢃꢀš]Àꢁ ꢃꢁZÇꢃŒ}Pꢁvꢀš]}v }( íꢀ ÁZꢁv
µ•]vP !µlha{rî ꢀ• šZꢁ ꢂꢀšꢀoÇ•š ~Çꢀꢄoꢁ {ðU ꢁvšŒÇ ñ À•X ꢁvšŒÇ òU
9{L••X hvꢁ }( šZꢁ ‰}••]ꢄoꢁ ꢁƉoꢀvꢀš]}v• (}Œ šZ]• ]• šZꢀš ha{rî ]•
šZꢁ ꢄꢁššꢁŒ }Æ]ꢃꢀvš (}Œ šZꢁ }Æ]ꢃꢀš]}v }( šZꢁ !µtI •‰ꢁꢂ]ꢁ• šZꢀv
Ç9athX .ꢀ•ꢁꢃ }v šZꢁ ꢀ(}Œꢁuꢁvš]}vꢁꢃ Œꢁ•µoš•U Áꢁ ꢂ}v•]ꢃꢁŒ
šZꢀš ha{rî ꢂꢀv ꢀꢂš ꢀ• ꢀv ꢁoꢁꢂšŒ}vršŒꢀv•(ꢁŒ uꢁꢃ]ꢀš}Œ ꢄꢁšÁꢁꢁv
!µ vꢀv}‰ꢀŒš]ꢂoꢁ• ꢀvꢃ hîX /}v•ꢁ‹µꢁvšoÇU !µlha{rî ꢁÆZ]ꢄ]šꢁꢃ
Z]PZꢁŒ ꢂꢀšꢀoÇš]ꢂ ‰ꢁŒ(}Œuꢀvꢂꢁ šZꢀv }šZꢁŒ •µ‰‰}Œšꢁꢃ !µ
vꢀv}‰ꢀŒš]ꢂoꢁ• ꢂꢀšꢀoÇ•š•U •µꢂZ ꢀ• !µl!oîhïU !µlÇ]hî ꢀvꢃ
!µl/ꢁhîU ꢀvꢃ šZ]• ]• o]lꢁoÇ ꢃꢁŒ]Àꢁꢃ (Œ}u šZꢁ ꢀꢄ]o]šÇ }( šZꢁ ha{r
î •µ‰‰}Œš š} ꢁ((ꢁꢂš]ÀꢁoÇ }Æ]ꢃ]Ìꢁ šZꢁ !µtI •‰ꢁꢂ]ꢁ•X
N
N
Bn
O
Bn
O
4b,c,d
99
97
O
O
O
O
F
F
5b,c,d
90
90
90
90
20
24
99 93(72)
1e
2e
O
O
O
O
6c,e
>99
76
95
90
1f
2f
O
O
O
O
7b,c,e
24
24
24
99
1g
2g
O
O
Ph
MeO
Ph
O
Ph
O
MeO
8b,c,f
>99
O
O
Ph
1h
2h
O
O
O
O
9b,c,e
90
97 85(68)
1i
2i
OH
OH
O
O
10b,c,e,h
1j
90
80
24
71 60(54)
2j
S
S
O
O
N
N
N
11b,c
0.5
93
93
1k
2k
O
O
12g,h
13b,g
90
24
12
82
74
41k
13l
EtO
EtO
N
1l
2l
IꢁŒꢁU Áꢁ ‰Œ}‰}•ꢁ ꢀ ‰}••]ꢄoꢁ Œꢁꢀꢂš]}v uꢁꢂZꢀv]•u (}Œ šZꢁ
!µlha{rîrꢂꢀšꢀoÇÌꢁꢃ }Æ]ꢃꢀš]Àꢁ rUtrꢃꢁZÇꢃŒ}Pꢁvꢀš]}v }( tr
N
N
110
N
N
ZꢁšꢁŒ}ꢀš}ur•µꢄ•š]šµšꢁꢃ
lꢁš}vꢁ•
~{ꢂZꢁuꢁ í•X
Lv]š]ꢀooÇU
1m
2m
Ph
Ph
•µ‰‰}Œšꢁꢃ !µ vꢀv}‰ꢀŒš]ꢂoꢁ• }Æ]ꢃ]Ìꢁ šZꢁ /tó ~ó A bU hU {• ꢄ}vꢃ
]v ꢀ •µꢄ•šŒꢀšꢁ š} ‰Œ}ꢃµꢂꢁ ꢀ ꢂꢀš]}v ~]u]v]µuU }Æ}v]µuU }Œ
•µo(}v]µu• ]všꢁŒuꢁꢃ]ꢀšꢁVîï šZꢁ trZÇꢃŒ}Pꢁv ]• ꢁo]u]vꢀšꢁꢃ ꢀ• ꢀ
ZÇꢃŒ]ꢃꢁ •‰ꢁꢂ]ꢁ• ‰}••]ꢄoÇ šZŒ}µPZ šZꢁ ꢂ}v•ꢁꢂµš]Àꢁ šÁ}
ꢁoꢁꢂšŒ}v• ꢀvꢃ }vꢁ ‰Œ}š}v šŒꢀv•(ꢁŒU ꢀvꢃ !µtI •‰ꢁꢂ]ꢁ• ]• (}Œuꢁꢃ
~{ꢂZꢁuꢁ íU •šꢁ‰ í•X !• ꢀꢄ}Àꢁruꢁvš]}vꢁꢃU šZꢁ ha{rî •µ‰‰}Œš
}Æ]ꢃ]Ìꢁ• šZꢁ !µtI •‰ꢁꢂ]ꢁ•U ꢀvꢃ šZꢁv hî Œꢁ}Æ]ꢃ]Ìꢁ• šZꢁ Œꢁꢃµꢂꢁꢃ
ha{rîX ÇZꢁ ꢂꢀš]}v ]všꢁŒuꢁꢃ]ꢀšꢁ ]• ꢂ}vÀꢁŒšꢁꢃ ]vš} šZꢁ ꢃꢁ•]Œꢁꢃ
rUtrµv•ꢀšµŒꢀšꢁꢃ lꢁš}vꢁ À]ꢀ ZÇꢃŒꢀš]}v (}oo}Áꢁꢃ ꢄÇ 9íꢂ.
ꢁo]u]vꢀš]}v ~{ꢂZꢁuꢁ íU •šꢁ‰ î ꢀvꢃ •šꢁ‰ ï•U }Œ À]ꢀ ꢃ]Œꢁꢂš
šꢀµš}uꢁŒ]Ìꢀš]}v ~{ꢂZꢁuꢁ íU •šꢁ‰ î[•X ÇZ]• Œꢁꢀꢂš]}v uꢁꢂZꢀv]•u ]•
ꢀ wꢁꢀꢂš]}v ꢂ}vꢃ]š]}v•W í ~ìXñ uu}o•U !µlha{rî ~!µW ïXò u}o9•U Iîh ~î u[•U ꢀ]Œ
~í ꢀšu•X /}vÀꢁŒ•]}v• ꢀvꢃ Ç]ꢁoꢃ• ÁꢁŒꢁ ꢃꢁšꢁŒu]vꢁꢃ ꢄÇ D/ ꢀvꢀoÇ•]•X ÇZꢁ Àꢀoµꢁ• ]v
‰ꢀŒꢁvšZꢁ•ꢁ• ꢀŒꢁ šZꢁ Ç]ꢁoꢃ• }( ]•}oꢀšꢁꢃ ‰Œ}ꢃµꢂš•X ꢄ hî ~í ꢀšu•X ꢃ [].Œ ~í u}o9•X
ꢂ IîhlíUðrꢃ]}Æꢀvꢁ ~íXõ u[lìXí u[•X ꢁ IîhlíUðrꢃ]}Æꢀvꢁ ~í u[lí u[•X ( IîhlbU br
ꢃ]uꢁšZÇoꢀꢂꢁšꢀu]ꢃꢁ ~í u[lí u[•X P bUbrꢃ]uꢁšZÇoꢀꢂꢁšꢀu]ꢃꢁX ~î u[• Z !µlha{rî
~!µW óXî u}o9•X ] L•}oꢀšꢁꢃ ꢀ• ꢀ u]ÆšµŒꢁ }( ŒꢁP]}]•}uꢁŒ•X ÇZꢁ ]•}uꢁŒ Œꢀš]} Áꢀ•
ꢃꢁšꢁŒu]vꢁꢃ ꢄÇ íI baw ꢀvꢀoÇ•]•X i ò]ꢁoꢃ Áꢀ• ꢃꢁšꢁŒu]vꢁꢃ ꢄÇ It[/ ꢀvꢀoÇ•]•X l 9šZÇo
ïr~(}ouÇouꢁšZÇoꢀu]v}•‰Œ}‰]}vꢀšꢁ Áꢀ• (}Œuꢁꢃ ]v ïò9 Ç]ꢁoꢃX o ïr
~tZꢁvÇoꢀu]v}•‰Œ}‰ꢀvꢁv]šŒ]oꢁ Áꢀ• (}Œuꢁꢃ ]v íõ9 Ç]ꢁoꢃX
írZÇꢃŒ}ÆÇrîUîUòUòršꢁšŒꢀuꢁšZÇo‰]‰ꢁŒ]ꢃ]vꢁ
~Ç9athI•
Áꢀ•
(}Œuꢁꢃ ]v òì9 Ç]ꢁoꢃ ~ꢄꢀ•ꢁꢃ }v Ç9ath•X ÇZ]• íWî îꢀlÇ9ath
ÇZ]• i}µŒvꢀo ]• ž ÇZꢁ w}Çꢀo {}ꢂ]ꢁšÇ }( /Zꢁu]•šŒÇ îìÆÆ
WX bꢀuꢁXU îìíïU ììU írï n ï
toꢁꢀ•ꢁ ꢃ} v}š ꢀꢃiµ•š uꢀŒP]v•

toꢁꢀ•ꢁ ꢃ} v}š ꢀꢃiµ•š uꢀŒP]v•
ChemComm
Page 4 of 4
View Article Online
DOI: 10.1039/C6CC07846J
/haaÜbL/!ÇLhb
W}µŒvꢀo bꢀuꢁ
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