2-Benzyloxymethyl-5-(tributylstannyl)tetrazole. A reagent for the preparation of 5-aryl- and 5-heteroaryl-1H-tetrazoles via the Stille reaction

Authors
Bookser, BC
Citation
Bc. Bookser, 2-Benzyloxymethyl-5-(tributylstannyl)tetrazole. A reagent for the preparation of 5-aryl- and 5-heteroaryl-1H-tetrazoles via the Stille reaction, TETRAHEDR L, 41(16), 2000, pp. 2805-2809
Citations number
20
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
16
Year of publication
2000
Pages
2805 - 2809
Database
ISI
SICI code
0040-4039(20000415)41:16<2805:2ARFTP>2.0.ZU;2-#
Abstract
2-Benzyloxymethyl-5-(tributylstannyl)tetrazole (2) is a useful reagent for the conversion of aryl- and heteroarylhalides (bromides and iodides) to 5-a ryl- and 5-heteroaryl-1H-tetrazoles. The conversion entails a copper(I) iod ide co-catalyzed Stille palladium-catalyzed cross-coupling reaction and a N -benzyloxymethyl deprotection step. Coupling was possible with electron neu tral and electron poor substrates in yields ranging from 35-93%. (C) 2000 E lsevier Science Ltd. All rights reserved.