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1,3,5‐Triaza‐7‐phosphaadamantane (PTA): A Practical and Versatile Nucleophilic Phosphine Organocatalyst
Author(s) -
Tang Xiaofang,
Zhang Bo,
He Zhengrong,
Gao Ruili,
He Zhengjie
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700071
Subject(s) - chemistry , nucleophile , phosphine , electrophile , catalysis , tributylphosphine , organic chemistry , adduct , combinatorial chemistry , medicinal chemistry , cycloaddition , nucleophilic addition
In this paper, the air‐stable and readily available 1,3,5‐triaza‐7‐phosphaadmantane (PTA) is reported as a practical and versatile nucleophilic phosphine organocatalyst. Under the mediation of 15–30 mol % of PTA, various electrophiles like aldehydes and imines readily undergo the Morita–Baylis–Hillman reactions with a variety of activated olefins, giving the corresponding adducts in high yields. In the phosphine‐catalyzed [3+2] cycloaddition reaction of 4‐substituted 2,3‐butadienoates with N ‐tosylimines, PTA is also proven to be a comparable catalyst as tributylphosphine (PBu 3 ). By systematic comparison with other structurally similar N,P catalysts, it is concluded that the superiority of PTA in the above nucleophilic catalysis is attributable to its comparable nucleophilicity with that of trialkylphosphines. The feasibility to use PTA as an alternative catalyst in place of the air‐sensitive trialkylphosphines is also discussed.