{[[K.18-Crown-6]Br3}n: A tribromide catalyst for the catalytic protection of amines and alcohols

Article abstract of DOI:10.1016/S1872-2067(12)60644-5

{[K.18-Crown-6]Br₃}_n, a unique tribromide-type catalyst, was utilized for the N-boc protection of amines and trimethylsilylation (TMS) and tetrahydropyranylation (THP) of alcohols. The method is general for the preparation of N-boc derivatives of aliphatic (acyclic and cyclic) and aromatic, and primary and secondary amines and also various TMS-ethers and THP-ethers. The simple separation of the catalyst from the product is one of the many advantages of this method.

Full text of DOI:10.1016/S1872-2067(12)60644-5

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GholamabbasꢀChehardoliꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ34ꢀ(2013)ꢀ1730–1733ꢀ
Tableꢁ2ꢁ
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ꢂ,"ꢁ 2&#ꢁ .0-"3!21ꢁ 5#0#ꢁ - 2ꢂ',#"ꢁ 5'2&ꢁ +-"#0ꢂ2#ꢁ 2-ꢁ #6!#**#,2ꢁ
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&&#ꢁ ꢂ32&-01ꢁ ꢂ!),-5*#"%#ꢁ $',ꢂ,!'ꢂ*ꢁ 13..-02ꢁ $-0ꢁ 2&'1ꢁ 5-0)ꢁ
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-!'#,!#1QꢁKꢂ+#"ꢂ,Qꢁ'T%Tꢁ'0ꢂ,ꢁꢂ,"ꢁ.ꢂ02'ꢂ*ꢁ13..-02ꢁ-$ꢁ2&'1ꢁ5-0)ꢁ 7ꢁ
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RO SiMe
3
R
O
O
Referencesꢁ
HMDS
DHP
{[K.18-crown-6]Br }
3
n
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Solvent
R-OH
R-OH
ꢈTꢉ K3ꢂ,%ꢁZꢁ,Qꢁꢀ&ꢂ,%ꢁ-ꢁKTꢁSynlettQꢁTRRWSꢁTTWYꢁ
ꢈUꢉ #0ꢂ7ꢁꢀꢁHꢁ 0Qꢁ,ꢂ007ꢁUQꢁꢆ'," #0%ꢁ(ꢁ QꢁK-312-,ꢁ&ꢁ$TꢁTetrahedronꢀLettQꢁ
Diboc
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ꢈXꢉ '8ꢂ22ꢁ%ꢁ2Qꢁ3ꢂ5*ꢂ)ꢁUQꢁ,0ꢂ"1&ꢂ5ꢁ ꢁ-Qꢁ,03#,',%ꢁ%ꢁꢆTꢀChemꢀRevQꢁS[[SQꢁ
[SSꢁSYTSꢁ
R
R
2
2
O
R
N
1
R
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ꢀ
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ꢈZꢉ ,-0')ꢂ0ꢁ-ꢁ3QꢁCꢂ,'#*ꢁ&Qꢁ3ꢂ3*ꢁDTꢁTetrahedronꢀLettQꢁTRR[QꢁWRSꢁSRRYꢁ ꢁ

ꢀ
GholamabbasꢀChehardoliꢀetꢀal.ꢀ/ꢀChineseꢀJournalꢀofꢀCatalysisꢀ34ꢀ(2013)ꢀ1730–1733ꢁ
ꢀ
ꢀ
GraphicalꢁAbstractꢀ
Chin.ꢀJ.ꢀCatal.QꢁTRSUQꢁUVSꢁSYURꢅSYUUꢁ ꢁ ꢁ "-'SꢁSRTSRSXꢋ-SZYTVTRXYꢃSTꢄXRXVVVW
{[K.18ꢀCrownꢀ6]Br3}n:ꢁAꢁtribromideꢁcatalystꢁforꢁtheꢁcatalyticꢁprotectionꢁofꢁaminesꢁ
andꢁalcoholsꢁ
ꢁ
#&-*ꢂ+ꢂ ꢂ1ꢁꢀ&#&ꢂ0"-*'#Qꢁ2-&ꢂ++ꢂ"ꢁ$*'ꢁZ-*$'%-*Qꢁ*ꢂ2#+#ꢁC#0ꢂ)&1&ꢂ,.ꢂ,ꢂ&ꢁ
HamedanꢀUniversityꢀofꢀMedicalꢀSciences,ꢀHamedan,ꢀIran;ꢀ ꢀ
BuꢁAliꢀSinaꢀUniversity,ꢀHamedan,ꢀIranꢀ
RO SiMe3
R
O
O
ꢀ
ꢀ
ꢀ
HMDS
DHP
{[K.18-crown-6]Br3}n
+
Solvent
R-OH
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