Substrate-promoted copper-catalyzed N-arylation of amino alcohols with aryl iodides in water

Article abstract of DOI:10.1016/S1872-2067(12)60623-8

An efficient method has been developed for the N-arylation of a variety of water-soluble amino alcohols (1.2 mmol) with aryl iodides (1.0 mmol) in water under CuI-catalyzed conditions. The reaction was conducted via substrate-promoted action and did not require an additional ligand or phase-transfer catalyst, and afforded the desired N-aryl amines in acceptable to excellent yields (64%-93%) under mild reaction conditions with a small excess of the amino alcohol.

Full text of DOI:10.1016/S1872-2067(12)60623-8

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NVꢂ07*ꢂ2'-,ꢁ -$ꢁ ꢂ+',-ꢁ ꢂ*!-&-*1ꢁ ꢂ,"ꢁ "'ꢂ+',#1ꢁ 5'2&ꢁ ꢂ07*ꢁ &ꢂ*'"#1ꢁ
TVꢉꢃVV2#2&-67.&#,7*ꢄꢂ+',-ꢊ#2&ꢂ,-*ꢁ ꢃ3eꢄꢁ ꢉUUꢊꢁ Kꢁ )2%ꢁ
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ꢂ,"V$0##ꢁꢂ,"ꢁ1-*4#,2V$0##ꢁ!-,"'2'-,1Qꢁꢂ*2&-3%&ꢁ2&#ꢁ0#/3'0#+#,2ꢁ
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UKꢄQꢁUTURꢁꢃ2QꢁTKQꢁJꢀ-ꢁWTTꢁK8ꢄTꢁ
ꢁ S
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0#.0#1#,2#"ꢁꢂꢁ1'%,'$'!ꢂ,2ꢁ*'+'2ꢂ2'-,ꢁ2-ꢁ2&#ꢁ%#,#0ꢂ*ꢁꢂ..*'!ꢂ2'-,ꢁ-$ꢁ
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2&'1ꢁꢂ..0-ꢂ!&ꢁꢉUWꢊTꢁK#0#',Qꢁ5#ꢁ"#1!0' #ꢁ2&#ꢁ"#4#*-.+#,2ꢁ-$ꢁꢂꢁ
,#5ꢁ!ꢂ2ꢂ*72'!ꢁ1712#+ꢁ2&ꢂ2ꢁ!ꢂ,ꢁ #ꢁꢂ..*'#"ꢁ2-ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁ
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STZTꢁꢃ+QꢁTKꢄTꢁ
ꢁ S
ꢂ+',-ꢁ ꢂ*!-&-*1ꢁ 31',%ꢁ ꢀ3'ꢁ ',ꢁ 5ꢂ2#0ꢁ ꢂ!!-0"',%ꢁ 2-ꢁ ꢂꢁ 13 V
VV3&#,7*ꢂ+',-VSV 32ꢂ,-*ꢁ ꢃ3gꢄꢁ ꢉU[ꢊ Kꢁ )2%ꢁ ꢃURRꢁ 2K8Qꢁ
120ꢂ2#V.0-+-2#"ꢁ ꢂ!2'-,Qꢁ 5'2&-32ꢁ 2&#ꢁ ,##"ꢁ $-0ꢁ ꢂ,ꢁ ꢂ""'2'-,ꢂ*ꢁ
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STXYꢁꢃ+QꢁVKꢄTꢁ
2.ꢁ ꢁ Experimentalꢁ
SV3&#,7*ꢂ+',-VTV.0-.ꢂ,-*ꢁꢃ3hꢄꢁSKꢁ)2%ꢁꢃWRRꢁ2K8QꢁꢀCꢀ*Uꢄꢁ
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ꢀ-..#0ꢃ'ꢄꢁ '-"'"#ꢁ ꢃ[Y$Qꢁ $',#ꢁ .-5"#0ꢄꢁ 5ꢂ1ꢁ .30!&ꢂ1#"ꢁ $0-+ꢁ
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SU
-&ꢂ,%&ꢂ'ꢁ-',.#3-ꢁ*',#ꢁꢀ&#+'!ꢂ*ꢁꢃ-&ꢂ,%&ꢂ'Qꢁꢀ&',ꢂꢄTꢁ3-2ꢂ11'3+ꢁ
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ꢀCꢀ*UꢄꢁTRTYQꢁWSTVQꢁXXTSQꢁSSUTSQꢁSSYTXQꢁST[TSQꢁSVZTRTꢁ
S
ꢃ-&ꢂ,%&ꢂ'Qꢁꢀ&',ꢂꢄTꢁ$**ꢁ-$ꢁ2&#ꢁꢂ07*ꢁ'-"'"#1ꢁꢂ,"ꢁꢂ+',#1ꢁ5#0#ꢁ.30V
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!&ꢂ1#"ꢁ$0-+ꢁ$*ꢂ""',ꢁꢀ&#+'1207ꢁꢀ-Tꢁꢇ2"Tꢁꢃ-&ꢂ,%&ꢂ'Qꢁꢀ&',ꢂꢄTꢁ$**ꢁ
ꢀCꢀ*UꢄꢁꢂꢁYTSVꢁꢃ2QꢁTKQꢁJꢀ-ꢁYTZꢁK8ꢄQꢁXTXZꢁꢃ2QꢁSKQꢁJꢀ-ꢁYTZꢁK8ꢄQꢁXTXUꢁꢃ"Qꢁ
-$ꢁ2&#ꢁ!-++#0!'ꢂ**7ꢁ1-30!#"ꢁ+ꢂ2#0'ꢂ*1ꢁ5#0#ꢁ31#"ꢁ5'2&-32ꢁ$30V
2&#0ꢁ .30'$'!ꢂ2'-,Tꢁ **ꢂ1&ꢁ !-*3+,ꢁ !&0-+ꢂ2-%0ꢂ.&7ꢁ 5ꢂ1ꢁ .#0V
TKQꢁJꢀ-ꢁYTZꢁK8ꢄQꢁUTYTꢁꢃ""QꢁSKQꢁJꢀ-ꢁWTSꢁK8QꢁJꢀ-ꢁSRT[ꢁK8ꢄQꢁUTWꢁꢃ""QꢁSKQꢁJꢀ
-ꢁWTSꢁK8QꢁJꢀ-ꢁSRT[ꢁK8ꢄQꢁUTUZꢁꢃ+QꢁSKꢄQꢁSTWXꢁꢃ+QꢁTKꢄQꢁRT[Vꢁꢃ2QꢁUKQꢁJꢀ-ꢁ
S
0#1'"3ꢂ*ꢁ"#32#0ꢂ2#"ꢁ1-*4#,2ꢁ.#ꢂ)1Tꢁ$**ꢁ-$ꢁ2&#ꢁ7'S#U*"1ꢁ0#.-02#"ꢁ',ꢁ
$-0+#"ꢁ5'2&ꢁ1'*'!ꢂꢁ%#*ꢁꢃTURꢅVRRꢁ+#1&ꢄTꢁ Kꢁꢂ,"ꢁ ꢀꢁ)2%ꢁ1.#!20ꢂꢁ
YTWꢁK8ꢄTꢁ ꢁ
S
5#0#ꢁ0#!-0"#"ꢁ-,ꢁꢂꢁDꢂ0'ꢂ,ꢁURRꢁ-0ꢁWRRꢁ2K8ꢁ',1203+#,2ꢁꢃ3ꢂ*-ꢁ
TVꢃUV,0-+-.&#,7*ꢂ+',-ꢄVSV 32ꢂ,-*ꢁꢃ3jꢄꢁ Kꢁ)2%ꢁꢃURRꢁ2K8Qꢁ
ꢀCꢀ*UꢄꢁꢂꢁXT[[ꢁꢃ2QꢁSKQꢁJꢀ-ꢁZTRꢁK8ꢄQꢁXTZTꢁꢃ+QꢁSKꢄQꢁXTYZꢁꢃ2QꢁSKQꢁJꢀ-ꢁTTRꢁ
K8ꢄQꢁXTWWꢁꢃ+QꢁSKꢄQꢁUTYTꢁꢃ+QꢁSKꢄQꢁUTWUꢁꢃ+QꢁSKꢄQꢁUTUWꢁꢃ+QꢁSKꢄQꢁSTWYꢁ
$*2-Qꢁ $+#0'!ꢂꢄꢁ 5'2&ꢁ !&#+'!ꢂ*ꢁ 1&'$21ꢁ 0#.-02#"ꢁ 0#*ꢂ2'4#ꢁ 2-ꢁ 2&#ꢁ
2&#ꢁ*'2#0ꢂ230#Tꢁ
TVꢃUV&-*7*ꢂ+',-ꢄ 32ꢂ,VSV 32SꢂU,-*ꢁ ꢃ3kꢄꢁ SKꢁ )2%ꢁ ꢃURRꢁ 2K8Qꢁ
ꢃ+QꢁTKꢄQꢁRT[Xꢁꢃ2QꢁUKQꢁJꢀ-ꢁYTWꢁK8ꢄRꢁ ꢀꢁ)2%ꢁꢃYWꢁ2K8QꢁꢀCꢀ*UꢄꢁSRTWQꢁ
2&#ꢁ !300#,2ꢁ 123"7ꢁ 0#.0#1#,2ꢁ ꢂ,ꢁ ꢂ4#0ꢂ%#ꢁ -$ꢁ ꢂ2ꢁ *#ꢂ12ꢁ 25-ꢁ ',"#V
.#,"#,2ꢁ 03,1Tꢁ &&#ꢁ ),-5,ꢁ !-+.-3,"1ꢁ 5#0#ꢁ !&ꢂ0ꢂ!2#0'8#"ꢁ 7ꢁ
TVTYQꢁWXTWQꢁXUTZQꢁSSTTTQꢁSSXTSQꢁSTRTVQꢁSTUTUQꢁSURTWQꢁSV[TURꢁ(-'V2-ꢁ
5'2&ꢁ'-"- #,8#,S#1ꢁ5ꢂ1ꢁꢂ1ꢁ$-**-51Tꢁ
&
!-+.ꢂ0',%ꢁ2&#'0ꢁ Kꢁ)2%ꢁ"ꢂ2ꢂꢁ5'2&ꢁ2&-1#ꢁ.0#4'-31*7ꢁ0#.-02#"ꢁ',ꢁ
M0ꢌZꢁTVVT[ꢌTVXT[ꢁꢃSSSꢄꢁꢉ2K ꢊTꢁ
&&#ꢁ%#,#0ꢂ*ꢁ.0-!#"30#ꢁ$-0ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁꢂ+',-ꢁꢂ*!-&-*1ꢁ
ꢀCꢀ*UꢄꢁꢂꢁYTRWꢁꢃ+QꢁSKꢄQꢁXTWVꢁꢃ"QꢁSKQꢁJꢀ-ꢁYTXꢁK8ꢄQꢁXTVXꢁꢃ"QꢁTKQꢁJꢀ-ꢁYTXꢁ
K8ꢄQꢁUTYTꢁꢃ""QꢁSKQꢁJꢀ-ꢁVTTꢁK8QꢁJꢀ-ꢁSRTZꢁK8ꢄQꢁUTWꢁꢃ""QꢁSKQꢁJꢀ-ꢁWT[ꢁK8QꢁJꢀ
'-"- #,8#,#ꢁꢃSTRꢁ++-*ꢄQꢁꢂ+',-ꢁꢂ*!-&-*ꢁꢃSTTꢁ++-*ꢄQꢁꢀ3'ꢁꢃRTSꢁ
-ꢁSRTZꢁK8ꢄQꢁUTUZꢁꢃ+QꢁSKꢄQꢁTTTZꢁꢃ1QꢁUKꢄQꢁSTWVꢁꢃ+QꢁTKꢄQꢁRT[Wꢁꢃ2QꢁUKQꢁJꢀ
SU
++-*ꢄQꢁ U+Kꢁ ꢃTTRꢁ ++-*ꢄQꢁ ꢂ,"ꢁ KT+ꢁ ꢃSꢁ +*ꢄꢁ 5#0#ꢁ ꢂ""#"ꢁ 2-ꢁ ꢂꢁ
1!0#5V!ꢂ..#"ꢁ2#12ꢁ23 #Qꢁꢂ,"ꢁ2&#ꢁ0#13*2',%ꢁ+'6230#ꢁ5ꢂ1ꢁ12'00#"ꢁ
ꢂ2ꢁSRRꢁꢀꢀꢁ$-0ꢁSTꢁ&TꢁQ.-,ꢁ!-+.*#2'-,ꢁ-$ꢁ2&#ꢁ0#ꢂ!2'-,Qꢁ"#2#0+',#"ꢁ
-ꢁYTWꢁK8ꢄRꢁ ꢀꢁ)2%ꢁꢃYWꢁ2K8QꢁꢀCꢀ*UꢄꢁSRTWQꢁTVT[QꢁT[TYQꢁWXTYQꢁXVTSQꢁ
SSRTZQꢁ SSVTWQꢁ SSZTZQꢁ ST[TTQꢁ SU[TRQꢁ SVZTWRꢁ (-'V2-ꢁ M0ꢌZꢁ SZRTTꢁ
&
ꢉ2K ꢊTꢁ
ꢁ S
7ꢁ&ꢇꢀQꢁ2&#ꢁ0#ꢂ!2'-,ꢁ+'6230#ꢁ5ꢂ1ꢁ!--*#"ꢁ2-ꢁꢂ+ '#,2ꢁ2#+.#0ꢂV
NQNVC'+#2&7*VNꢂV.&#,7*#2&7*#,#VSQTV"'ꢂ+',#1ꢁ ꢃ3lꢄꢁ ꢉVRꢊ Kꢁ
230#ꢁꢂ,"ꢁ#620ꢂ!2#"ꢁ5'2&ꢁ#2&7*ꢁꢂ!#2ꢂ2#ꢁꢃUꢁ)ꢁWꢁ+*ꢄTꢁ&&#ꢁ!-+ ',#"ꢁ
-0%ꢂ,'!ꢁ.&ꢂ1#1ꢁ5#0#ꢁ2&#,ꢁ"0'#"ꢁ-4#0ꢁꢂ,&7"0-31ꢁ)ꢂT-+Vꢁ #$-0#ꢁ
)2%ꢁꢃWRRꢁ2K8QꢁꢀCꢀ*UꢄꢁꢂꢁYTS[ꢁꢃ"QꢁJꢀ-ꢁYTWꢁK8QꢁSKꢄQꢁXTYYꢁꢃ2QꢁJꢀ-ꢁYTTꢁ
K8QꢁSKꢄQꢁXTYUꢁꢃ"QꢁJꢀ-ꢁYT[ꢁK8QꢁSKꢄQꢁVTR[ꢁꢃ2QꢁJꢀ-ꢁXTZꢁK8QꢁSKꢄQꢁUTXYꢁꢃ"QꢁJꢀ

ꢀ
MingꢀJinꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ34ꢀ(2013)ꢀ1651–1655ꢁ
ꢀ
-ꢁWTSꢁK8QꢁSKꢄQꢁUTUSꢁꢃ2QꢁJꢀ-ꢁWTUꢁK8QꢁSKꢄQꢁTTZXꢁꢃ1QꢁUKꢄTꢁ
Tableꢁ2ꢁ ꢁ
S
ꢀ
TVꢃ3&#,7*ꢂ+',-ꢄ.&#,-*ꢁ ꢃ3mꢄꢁ ꢉVSꢊꢁ Kꢁ )2%ꢁ ꢃWRRꢁ 2K8Qꢁ
NVꢂ07*ꢂ2'-,ꢁ-$ꢁꢂ+',-ꢁꢂ*!-&-*1ꢁ5'2&ꢁ'-"- #,8#,#1ꢁ',ꢁ5ꢂ2#0T
ꢀCꢀ*UꢄꢁꢂꢁYTS[ꢁꢃ+QꢁUKꢄQꢁYTR[ꢁꢃ2QꢁJꢀ-ꢁZTRꢁK8QꢁSKꢄQꢁXT[Zꢁꢃ"QꢁJꢀ-ꢁZTRꢁK8Qꢁ
SKꢄQꢁXTZYꢁꢃ+QꢁTKꢄQꢁXTYYꢁꢃ"QꢁJꢀ-ꢁYTXꢁK8QꢁTKꢄQꢁWTYXꢁꢃ 0QꢁSKꢄQꢁWTTVꢁ
ꢃ 0QꢁSKꢄTꢁ
R2
R3
CuI 10 mol%
R2
R3
R1
KOH 2.0 eq.
R1
+
NH OH
H2O, 100 o
C
I
H2N
OH
12 h
S
TV3&#,-67 #,8#,ꢂ+',#ꢁ ꢃ3m'ꢄꢁ ꢉVSꢊꢁ Kꢁ )2%ꢁ ꢃURRꢁ 2K8Qꢁ
3a-3m
1
2
ꢁ
ꢀCꢀ*UꢄꢀꢂꢁWTT[ꢁꢃ 0QꢁTꢁKꢄQꢁXTSVꢁꢃ""QꢁSKQꢁJꢀ-ꢁXTZQꢁJꢀ-ꢁTTVꢁK8ꢄQꢁXTS[ꢁꢃ"Qꢁ
SKQꢁJꢀ-ꢁTTVꢁK8ꢄQꢁXTUUꢁꢃ"QꢁSKQꢁJꢀ-ꢁZTRꢁK8ꢄQꢁXT[YꢅYTRSꢁꢃ+QꢁUKꢄQꢁYTR[ꢁ
ꢃ2QꢁSKQꢁJꢀ-ꢁYTTꢁK8ꢄQꢁYTUXꢁꢃ2QꢁTKQꢁJꢀ-ꢁYTXꢁK8ꢄTꢁ
ꢂ
$07*ꢁ ꢁ
ꢆ'#*"ꢁ ꢁ
(,207
Sꢁ
$+',#ꢁꢃ2ꢄꢁ
30-"3!2ꢁꢃ3ꢄꢁ
&ꢂ*'"#ꢁꢃ1ꢄꢁ
ꢃ$ꢄꢁ
H2N
[Uꢁ
OH
ꢁ
OH
I
ꢁ
N
H
3a
3.ꢁ ꢁ Resultsꢁandꢁdiscussionꢁ
Br
Br
H2N
Tꢁ
Uꢁ
ZXꢁ
OH
ꢁ
OH
3.1.ꢀ ꢀ Optimizationꢀofꢀconditionsꢀꢀ
I
ꢁ
N
H
3b
Br
Br
&&#ꢁ !300#,2ꢁ 5-0)ꢁ $-!31#"ꢁ ','2'ꢂ**7ꢁ -,ꢁ 2&#ꢁ !-3.*',%ꢁ -$ꢁ
TVꢂ+',-VSV 32ꢂ,-*ꢁ 5'2&ꢁ '-"- #,8#,#ꢁ ꢂ1ꢁ ꢂꢁ +-"#*ꢁ 0#ꢂ!2'-,ꢁ 2-ꢁ
-.2'+'8#ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ!-,"'2'-,1Tꢁ$ꢁ4ꢂ0'#27ꢁ-$ꢁ"'$$#0#,2ꢁ ꢂ1#1ꢁꢃTꢁ
#/3'4Tꢄꢁꢂ,"ꢁꢀ3ꢁ1-30!#1ꢁꢃSRꢁ+-*$ꢄꢁ5#0#ꢁ1!0##,#"ꢁꢂ%ꢂ',12ꢁ2&#ꢁ
12ꢂ,"ꢂ0"ꢁ !-3.*',%ꢁ .0-!#"30#Qꢁ 5&'!&ꢁ ',4-*4#"ꢁ 2&#ꢁ 0#ꢂ!2'-,ꢁ -$ꢁ
'-"- #,8#,#ꢁꢃSꢁ#/3'4Tꢄꢁ5'2&ꢁTVꢂ+',-VSV 32ꢂ,-*ꢁꢃSTTꢁ#/3'4Tꢄꢁ',ꢁ
5ꢂ2#0ꢁ ꢃSꢁ +*ꢄTꢁ &&#ꢁ 0#13*21ꢁ -$ꢁ 2&#1#ꢁ 1!0##,',%ꢁ #6.#0'+#,21ꢁ ꢂ0#ꢁ
1&-5,ꢁ',ꢁ&ꢂ *#ꢁSTꢁ
H2N
H2N
H2N
[Rꢁ
OH
ꢁ
OH
I
ꢁ
ꢁ
N
H
3c
Vꢁ
ZXꢁ
OH
ꢁ
OH
I
N
H
3d
MeO
MeO
Wꢁ
Xꢁ
Yꢁ
Zꢁ
ZVꢁ
[Sꢁ
XYꢁ
YXꢁ
OH
ꢁ
+30ꢁ ','2'ꢂ*ꢁ 5-0)ꢁ $-!31#"ꢁ -,ꢁ 1!0##,',%ꢁ "'$$#0#,2ꢁ ꢂ1#1ꢁ
ꢂ%ꢂ',12ꢁ2&#ꢁ+-"#*ꢁNVꢂ07*ꢂ2'-,ꢁ0#ꢂ!2'-,ꢁ',ꢁ2&#ꢁ.0#1#,!#ꢁ-$ꢁꢀ3'ꢁ
ꢃRTSꢁ#/3'4TꢄTꢁ3*#ꢂ1',%*7Qꢁ2&#ꢁ0#ꢂ!2'-,ꢁ.0-!##"#"ꢁ5#**ꢁ5&#,ꢁU+Kꢁ
5ꢂ1ꢁ31#"ꢁꢂ1ꢁ2&#ꢁ ꢂ1#ꢁꢂ,"ꢁ%ꢂ4#ꢁ2&#ꢁ"#1'0#"ꢁ.0-"3!2ꢁ',ꢁꢂꢁ7'#*"ꢁ-$ꢁ
YW$ꢁ$-**-5',%ꢁSTꢁ&ꢁꢂ2ꢁZWꢁꢀꢀꢁꢃ&ꢂ *#ꢁSQꢁ#,207ꢁWꢄTꢁQ,$-023,ꢂ2#*7Qꢁ
2&#ꢁ31#ꢁ-$ꢁ-2&#0ꢁ ꢂ1#1ꢁ13!&ꢁꢂ1ꢁUU3+VQꢁUTꢀ+UQꢁꢀ1Tꢀ+UQꢁꢂ,"ꢁ)ꢂ+Kꢁ
0#13*2#"ꢁ',ꢁ*-5#0ꢁ7'#*"1ꢁꢃ&ꢂ *#ꢁSQꢁ#,20'#1ꢁSꢅVꢄTꢁ-#4#0ꢂ*ꢁ0#ꢂ"'*7ꢁ
ꢂ4ꢂ'*ꢂ *#ꢁ!-..#0ꢁ1ꢂ*21Qꢁ',!*3"',%ꢁꢀ3'Qꢁꢀ3T+Qꢁꢀ3,0ꢁꢂ,"ꢁꢀ3ꢀ*Qꢁ5#0#ꢁ
2&#,ꢁ #4ꢂ*3ꢂ2#"ꢁ 3,"#0ꢁ 2&#ꢁ U+Kꢁ !-,"'2'-,1ꢁ ꢃ&ꢂ *#ꢁ SQꢁ #,20'#1ꢁ
WꢅZꢄQꢁꢂ,"ꢁꢀ3'ꢁ5ꢂ1ꢁ$-3,"ꢁ2-ꢁ.0-4'"#ꢁ2&#ꢁ #12ꢁ0#13*21ꢁꢃ&ꢂ *#ꢁSQꢁ
#,207ꢁ WꢄTꢁ H#ꢁ 2&#,ꢁ .0-! ##"#"ꢁ 2-ꢁ ',4#12'%ꢂ2#ꢁ 2&#ꢁ #$$#! 21ꢁ -$ꢁ 2&#ꢁ
2#+.#0ꢂ230#ꢁꢂ,"ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ2'+#ꢁ-,ꢁ2&#ꢁ-32!-+#ꢁ-$ꢁ2&#ꢁ0#ꢂ!V
2'-,ꢁꢃ&ꢂ *#ꢁSQꢁ#,20'#1ꢁZꢅSRꢄTꢁ3*#ꢂ1',%*7Qꢁ5&#,ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ5ꢂ1ꢁ
!-,"3!2#"ꢁ ꢂ2ꢁ SRRꢁ ꢀꢀQꢁ 2&#ꢁ "#1'0#"ꢁ ꢂ+',ꢂ2'-,ꢁ .0-"3! 2ꢁ 5ꢂ1ꢁ - V
2ꢂ',#"ꢁ',ꢁZ[$ꢁ7'#*"ꢁꢃ&ꢂ *#ꢁSQꢁ#,207ꢁ[ꢄQꢁ0#.0#1#,2',%ꢁꢂꢁ1'%,'$'V
!ꢂ,2ꢁ',!0#ꢂ1#ꢁ $0-+ꢁ2&#ꢁ7'#*"ꢁ- 2ꢂ',#"ꢁ 5&#,ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ 5ꢂ1ꢁ
OH
I
ꢁ
N
H
3e
3f
H N
OH
2
ꢁ
I
I
I
ꢁ
N
OH
H
OH
H N
2
ꢁ
OH
ꢁ
ꢁ
N
H
3g
H N
2
OH
HO
ꢁ
N
H
3h
NH
2
2
[ꢁ
ꢁ
OH
ꢁ
OH
OH
Z[ꢁ
I
ꢁ
ꢁ
N
H
3i
Br
Br
NH
NH
SRꢁ
[Tꢁ
OH
ꢁ
I
I
N
H
3j
Tableꢁ1ꢁ ꢁ
-!0##,',%ꢁ-$ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ!-,"'2'-,1ꢁ$-0ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁTVꢂ+',-VSV
ꢁ
2
SSꢁ
XVꢁ
32ꢂ,-*ꢁ5'2&ꢁ'-"- #,8#,#Tꢁ
OH
N
ꢁ
ꢃXW$ Qꢁ
OH
N
!
N
ꢁ
[Z$ ꢄ
H
3k
H N
H
2
STꢁ
VXꢁ
N
ꢁ
ꢁ
ꢃVZ$ Qꢁ
I
I
ꢁ
ꢁ
ꢁ
ꢂꢀ
(,207
ꢀꢂ2ꢂ*712ꢁ
ꢀ3'ꢁ
,ꢂ1#ꢁ &#+.#0ꢂ230#ꢁꢃꢀꢀꢄꢁ &'+#ꢁꢃ&ꢄꢁ ꢆ'#*" ꢃ$ꢄ
!
3l
[W$ ꢄ
ꢁ
Sꢁ
UU3+Vꢁ
UTꢀ+Uꢁ
ꢀ1Tꢀ+Uꢁ
)ꢂ+Kꢁ
U+Kꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
STꢁ
STꢁ
STꢁ
STꢁ
STꢁ
STꢁ
UXꢁ
USꢁ
VUꢁ
XSꢁ
YWꢁ
XSꢁ
H
N
NH2
OH
SUꢁ
SZꢁ
Tꢁ
ꢀ3'ꢁ
ꢃTSSꢄ
ꢁ
Uꢁ
ꢀ3'ꢁ
OH
3m
O
ꢃS[$ Qꢁ
Vꢁ
ꢀ3'ꢁ
!
[X$ ꢄ
Wꢁ
ꢀ3'ꢁ
Xꢁ
ꢀ3T+ꢁ
U+Kꢁ
NH2
Yꢁ
ꢀ3,0ꢁ
ꢀ3ꢀ*ꢁ
ꢀ3'ꢁ
U+Kꢁ
U+Kꢁ
U+Kꢁ
U+Kꢁ
ꢁ ZWꢁ
ꢁ ZWꢁ
SRRꢁ
SRRꢁ
STꢁ
STꢁ
STꢁ
TRꢁ
XYꢁ
YTꢁ
Z[ꢁ
Z[ꢁ
Zꢁ
3m'
[ꢁ
%#ꢂ!2'-,1ꢁ .#0$-0+#"ꢁ 5'2&ꢁ $0'ꢁ ꢃSTRꢁ ++-*ꢄꢁ ꢂ,"G ꢂ+',-ꢁ ꢂ*!-&-*1ꢁ ꢃSTTꢁ
SRꢁ
ꢀ3'ꢁ
++-*ꢄꢁ',ꢁ5ꢂ2#0ꢁꢃSꢁ+*ꢄTꢁ
ꢂꢁ
'1-*ꢂ2#"ꢁ7'#*"Tꢁ
%#ꢂ!2'-,1ꢁ .#0$-0+#"ꢁ 5'2&ꢁ '-"- #,8#,#ꢁ ꢃSTRꢁ ++-*ꢄꢁ ꢂ,"ꢁ TVꢂ+',-VSV
ꢁ
ꢁ
ꢀ-,4#01'-,ꢁ-$ꢁ2&#ꢁ13 120ꢂ2#Tꢁ
32ꢂ,-*ꢁꢃSTTꢁ++-*ꢄꢁ',ꢁ5ꢂ2#0ꢁꢃSꢁ+*ꢄTꢁ
ꢂꢁ
!ꢁ
'1-*ꢂ2#"ꢁ7'#*"Tꢁ
-#*#!2'4'27ꢁ$-0ꢁ2&#ꢁ.0-"3!2Tꢁ

ꢀ
MingꢀJinꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ34ꢀ(2013)ꢀ1651–1655ꢀ
5#0#ꢁ - 2ꢂ',#"ꢁ *')#*7ꢁ #! ꢂ31#ꢁ -$ꢁ 2&#ꢁ .--0ꢁ 5ꢂ2#0ꢁ 1-*3 '*'27ꢁ -$ꢁ
2&#1#ꢁ13 120ꢂ2#1Qꢁ5&'!&ꢁ5-3*"ꢁ+ꢂ)#ꢁ'2ꢁ"'$$'!3*2ꢁ$-0ꢁ2&#+ꢁ2-ꢁ!-V
-0"',ꢂ2#ꢁ2-ꢁ2&#ꢁꢀ3ꢁ!#,2#0Tꢁ
3.3.ꢀ ꢀ Mechanisticꢀconsiderationꢀꢀ
,ꢂ1#"ꢁ-,ꢁ2&#ꢁ0#13*21ꢁ.0-4'"#"ꢁꢂ -4#Qꢁ5#ꢁ&ꢂ4#ꢁ.0-.-1#"ꢁꢂꢁ
13 120ꢂ2#ꢁ ꢃꢂ+',-ꢁ ꢂ*!-&-*ꢄV.0-+-2#"ꢁ !ꢂ2ꢂ*72'!ꢁ +#!&ꢂ,'1+ꢁ $-0ꢁ
2&#ꢁ !300#,2ꢁ *'%ꢂ,"V$0##ꢁ ꢂ/3#-31V.&ꢂ1#ꢁ 0#ꢂ!2'-,1ꢁ ꢃ-!&#+#ꢁ SꢄTꢁ
&&31Qꢁ 2&#ꢁ ꢂ+',-ꢁ ꢂ*!-&-*ꢁ '1ꢁ '1V,3!*#-.&'*'!ꢁ ꢂ,"ꢁ !ꢂ.ꢂ *#ꢁ -$ꢁ
$-0+',%ꢁ!&#*ꢂ2-0ꢁAꢁ5'2&ꢁꢀ3'Tꢁ-3 1#/3#,2ꢁ-6'"ꢂ2'4#ꢁꢂ""'2'-,ꢁ-$ꢁ
ꢂ,ꢁꢂ07*ꢁ&ꢂ*'"#ꢁ2-ꢁ!&#*ꢂ2-0ꢁAꢁ5-3*"ꢁ*#ꢂ"ꢁ2-ꢁ2&#ꢁ$-0+ꢂ2'-,ꢁ-$ꢁ',V
2#0+#"'ꢂ2#ꢁBQꢁ5&'!&ꢁ!-3*"ꢁ3,"#0%-ꢁ,3!*#-.&'*'!ꢁ13 12'232'-,ꢁ',ꢁ
2&#ꢁ.0#1#,!#ꢁ-$ꢁ ꢂ1#ꢁ2-ꢁ%'4#ꢁ!-+.*#6ꢁCTꢁ%#"3!2'4#ꢁ#*'+',ꢂ2'-,ꢁ
-$ꢁCꢁ!-3*"ꢁ2&#,ꢁ%'4#ꢁ0'1#ꢁ2-ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ.0-"3!2ꢁꢉVTꢊTꢁ
ꢁ
Schemeꢁ 1.ꢁ 30-.-1#"ꢁ 131 20ꢂ2#V.0-+-2#"ꢁ +#! &ꢂ,'1+ꢁ $-0ꢁ ! -.V
.#0V!ꢂ2ꢂ*78#"ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁꢂ+',-ꢁꢂ*!-&-*1Tꢁ
!-,"3!2#"ꢁꢂ2ꢁZWꢁꢀꢀꢁꢃ&ꢂ *#ꢁSQꢁ#,207ꢁWꢄTꢁ&&#ꢁ#62#,1'-,ꢁ-$ꢁ2&#ꢁ0#V
4.ꢁ ꢁ Conclusionsꢁ
ꢂ!2'-,ꢁ2'+#ꢁ2-ꢁTRꢁ&Qꢁ&-5#4#0Qꢁ"'"ꢁ,-2ꢁ0#13*2ꢁ',ꢁꢂ,7ꢁ$302&#0ꢁ',V
!0#ꢂ1#ꢁ',ꢁ2&#ꢁ0#ꢂ!2'-,ꢁ7'#*"ꢁꢃ&ꢂ *#ꢁSQꢁ#,207ꢁSRꢄTꢁ&ꢂ)#,ꢁ2-%#2&#0Qꢁ
2&#1#ꢁ0#13*21ꢁ2&#0#$-0#ꢁ',"'!ꢂ2#"ꢁ2&ꢂ2ꢁ2&#ꢁ-.2'+'8#"ꢁ.0-!#"30#ꢁ
$-0ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁTVꢂ+',-VSV 32ꢂ,-*ꢁ0#/3'0#"ꢁ2&#ꢁꢂ..*'!ꢂV
2'-,ꢁ-$ꢁꢀ3'ꢁꢂ1ꢁꢂꢁ!ꢂ2ꢂ*712ꢁꢂ,"ꢁU+Kꢁꢂ1ꢁꢂꢁ ꢂ1#ꢁ',ꢁ5ꢂ2#0ꢁꢂ2ꢁSRRꢁꢀꢀꢁ
ꢃ&ꢂ *#ꢁSQꢁ#,207ꢁ[ꢄTꢁ
H#ꢁ &ꢂ4#ꢁ 13!!#11$3**7ꢁ "#4#*-.#"ꢁ ꢂꢁ ,#5ꢁ +#2&-"ꢁ $-0ꢁ 2&#ꢁ
ꢂ/3#-31ꢁ.&ꢂ1#ꢁ!-..#0V!ꢂ2ꢂ*78#"ꢁNVꢂ07*ꢂ2'-,ꢁ-$ꢁꢂ+',-ꢁꢂ*!-&-*1ꢁ
2&ꢂ2ꢁ"-#1ꢁ,-2ꢁ0#/3'0#ꢁꢂ,ꢁꢂ""'2'-,ꢂ*ꢁ*'%ꢂ,"Qꢁ.&ꢂ1#V20ꢂ,1$#0ꢁ!ꢂ2ꢂV
*712Qꢁ -0ꢁ +'!0-5ꢂ4#ꢁ '00ꢂ"'ꢂ2'-,Tꢁ &&#ꢁ 0#ꢂ!2'-,1ꢁ .0-!##"#"ꢁ
1+--2&*7ꢁꢂ,"ꢁ#$$'!'#,2*7ꢁ',ꢁ+-12ꢁ!ꢂ1#1ꢁ2-ꢁꢂ$$-0"ꢁ2&#ꢁNVꢂ07*ꢂ2'-,ꢁ
.0-"3!21ꢁ ',ꢁ &'%&ꢁ 7'#*"1ꢁ 3,"#0ꢁ +'*"ꢁ 0#ꢂ!2'-,ꢁ !-,"'2'-,1ꢁ 5'2&ꢁ
3.2.ꢀ ꢀ Substrateꢀscopeꢀofꢀaminoꢀalcoholsꢀandꢀarylꢀiodidesꢀ
ꢀ
-,*7ꢁꢂꢁ1+ꢂ**ꢁ#6!#11ꢁ-$ꢁ2&#ꢁꢂ+',-ꢁꢂ*!-&-*Tꢁ*302&#0ꢁ123"'#1ꢁꢂ'+#"ꢁ
ꢂ2ꢁ #6.ꢂ,"',%ꢁ2&#ꢁ 1!-.#ꢁ-$ꢁ2&'1ꢁ .0-2-!-*ꢁ2-ꢁ-2&#0ꢁ,'20-%#,ꢁ,3V
!*#-.&'*#1Qꢁꢂ1ꢁ5#**ꢁꢂ1ꢁ"#4#*-.',%ꢁꢂꢁ"##.#0ꢁ3,"#012ꢂ,"',%ꢁ-$ꢁ2&#ꢁ
0#ꢂ!2'-,ꢁ+#!&ꢂ,'1+Qꢁꢂ0#ꢁ!300#,2*7ꢁ3,"#05ꢂ7ꢁ',ꢁ-30ꢁ*ꢂ -0ꢂ2-07Tꢁ
H'2&ꢁ 2&#ꢁ -.2'+'8#"ꢁ 0#ꢂ!2'-,ꢁ !-,"'2'-,1ꢁ ',ꢁ &ꢂ,"Qꢁ 5#ꢁ .0-V
!##"#"ꢁ2-ꢁ',4#12'%ꢂ2#ꢁ2&#ꢁ1!-.#ꢁ-$ꢁ2&'1ꢁ0#ꢂ!2'-,ꢁ31',%ꢁꢂꢁ4ꢂ0'#27ꢁ
-$ꢁ"'$$#0#,2ꢁꢂ+',-ꢁꢂ*!-&-*1ꢁꢂ,"ꢁꢂ07*ꢁ'-"'"#1Tꢁ&&#ꢁ0#13*21ꢁ-$ꢁ2&'1ꢁ
5-0)ꢁꢂ0#ꢁ13++ꢂ0'8#"ꢁ',ꢁ&ꢂ *#ꢁTTꢁ$**ꢁ-$ꢁ2&#ꢁ.0-"3!21ꢁ0#13*2',%ꢁ
Acknowledgmentsꢁ
S
$0-+ꢁ2&#1#ꢁ#6.#0'+#,21ꢁ5#0#ꢁ!&ꢂ0ꢂ!2#0'8#"ꢁ 7ꢁ Kꢁ)2%ꢁꢂ,"ꢁ2-Qꢁ
ꢂ,"ꢁ 5#0#ꢁ !-,1'12#,2ꢁ 5'2&ꢁ 2&#ꢁ *'2#0ꢂ230#ꢁ "ꢂ2ꢂTꢁ &&#ꢁ 0#13*21ꢁ ',ꢁ
&ꢂ *#ꢁ Tꢁ !*#ꢂ0*7ꢁ "#+-,120ꢂ2#ꢁ 2&#ꢁ 0-ꢂ"ꢁ 1!-.#ꢁ -$ꢁ 2&#ꢁ !300#,2ꢁ
&&#ꢁꢂ32&-01ꢁ5-3*"ꢁ*')#ꢁ2-ꢁꢂ!),-5*#"%#ꢁC0TꢁKꢂ,/',%ꢁC-,%ꢁ
$-0ꢁ&#*.$3*ꢁ"'1!311'-,1Tꢁ
.0-!#"30#Qꢁ5'2&ꢁꢂꢁ4ꢂ0'#27ꢁ-$ꢁ"'$$#0#,2ꢁꢂ+',-ꢁꢂ*!-&-*1Qꢁ13!&ꢁꢂ1ꢁ
#2&ꢂ,-*ꢂ+',#ꢁ ꢂ,"ꢁ UVꢂ+',-VSV.0-.ꢂ,-*Qꢁ %'4',%ꢁ 2&#ꢁ "#1'0#"ꢁ
Referencesꢁ
.0-"3! 21ꢁ ',ꢁ &'%&ꢁ 7'#*"1ꢁ ꢃ&ꢂ* #ꢁ TQꢁ #,20'#1ꢁ SꢅXꢄTꢁ H&#,ꢁ
VVꢂ+',- 32ꢂ,-*ꢁ5ꢂ1ꢁ31#"ꢁꢂ1ꢁꢂꢁ13 120ꢂ2#Qꢁꢂꢁ*-5#0ꢁ7'#*"ꢁ-$ꢁXY$ꢁ
5ꢂ1ꢁ- 2ꢂ',#"ꢁꢃ&ꢂ *#ꢁTQꢁ#,207ꢁYꢄTꢁ(4#,ꢁꢂ+',-ꢁꢂ*!-&-*1ꢁ #ꢂ0',%ꢁ
0ꢂ,!&#"ꢁ ꢂ*)7*ꢁ !&ꢂ',1ꢁ ꢂ$$-0"#"ꢁ 2&#ꢁ "#1'0#"ꢁ .0-"3!21ꢁ ',ꢁ &'%&ꢁ
7'#*"1ꢁꢃ&ꢂ *#ꢁTQꢁ#,20'#1ꢁZꢅSSꢄTꢁ$1ꢁ$-0ꢁ2&#ꢁꢂ07*ꢁ'-"'"#1Qꢁꢂꢁ0ꢂ,%#ꢁ-$ꢁ
"'$$#0#,2ꢁ13 12'23#,21ꢁ5ꢂ1ꢁ2-*#0ꢂ2#"Qꢁ',!*3"',%ꢁ 0-+-Qꢁ+#2&7*Qꢁ
ꢂ,"ꢁ+#2&-67ꢁ%0-3.1TꢁH&#,ꢁTVꢂ+',- 32ꢂ,-*ꢁ5ꢂ1ꢁ13 (#!2#"ꢁ2-ꢁ
2&#ꢁ-.2'+'8#"ꢁ0#ꢂ!2'-,ꢁ!-,"'2'-,1Qꢁ1'%,'$'!ꢂ,2ꢁ#*#!20-,'!ꢁ#$$#!21ꢁ
5#0#ꢁ- 1#04#"ꢁ$-0ꢁ2&#ꢁ#*#!20-,V.--0ꢁꢂ,"ꢁ#*#!20-,V0'!&ꢁ13 12'V
232#"ꢁꢂ07*ꢁ'-"'"#1ꢁꢃ&ꢂ *#ꢁTQꢁ#,20'#1ꢁSRꢁꢂ,"ꢁSSꢄTꢁ&&#ꢁ.0#1#,!#ꢁ-$ꢁ
ꢂ,ꢁ #*#!20-,V"-,ꢂ2',%ꢁ +#2&7*ꢁ -0ꢁ +#2&-67ꢁ %0-3.ꢁ *#"ꢁ 2-ꢁ *-5#0ꢁ
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