Synthesis 2015; 47(03): 323-329
DOI: 10.1055/s-0034-1379967
psp
© Georg Thieme Verlag Stuttgart · New York

Convenient and Direct Azidation of sec-Benzyl Alcohols by Trimethylsilyl Azide with Bismuth(III) Triflate Catalyst

Jumreang Tummatorn*
a  Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand   Email: [email protected]
b  Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
,
Charnsak Thongsornkleeb
a  Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand   Email: [email protected]
b  Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
,
Somsak Ruchirawat
a  Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand   Email: [email protected]
b  Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand
,
Phanida Thongaram
a  Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand   Email: [email protected]
,
Benyapa Kaewmee
a  Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 08 September 2014

Accepted after revision: 12 December 2014

Publication Date:
12 January 2015 (online)


Abstract

sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.

Supporting Information

 
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