磷杂金刚烷作为钯催化交叉偶联反应的配体：库的合成、表征以及在含有β-氢的卤代烃和甲苯磺酸酯与硼酸及烷基硼烷的铃木偶联反应中的筛选

Phosphaadamantanes as ligands for palladium catalyzed cross-coupling chemistry: library synthesis, characterization, and screening in the Suzuki coupling of alkyl halides and tosylates containing beta-hydrogens with boronic acids and alkylboranes.

作者信息

Brenstrum Tim, Gerristma David A, Adjabeng George M, Frampton Christopher S, Britten James, Robertson Alan J, McNulty James, Capretta Alfredo

机构信息

Department of Chemistry, McMaster University, Hamilton, Ontario L8S 4M1, Canada.

出版信息

J Org Chem. 2004 Oct 29;69(22):7635-9. doi: 10.1021/jo048875+.

DOI:10.1021/jo048875+

PMID:15497991

Abstract

A 15-member library of phosphaadamantane ligands has been prepared via P-arylation of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane. Screening of this tertiary phosphine collection has allowed for the rapid determination of the most suitable ligand, specifically 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane, for facilitating Suzuki-type couplings of alkyl halides or tosylates containing beta-hydrogens with either boronic acids or alkylboranes.

摘要

通过1,3,5,7-四甲基-2,4,8-三氧杂-6-磷杂金刚烷的P-芳基化反应制备了一个由15个磷杂金刚烷配体组成的文库。对该叔膦文库的筛选能够快速确定最适合的配体，即1,3,5,7-四甲基-6-(2,4-二甲氧基苯基)-2,4,8-三氧杂-6-磷杂金刚烷，以促进含β-氢的卤代烃或甲苯磺酸盐与硼酸或烷基硼烷的铃木型偶联反应。