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Highly Selective Preparation of Allenic and Homopropargylic Hydrazides through Regiospecific Addition of Propargyltrichlorosilane and Allenyltrichlorosilane to Various Types of N ‐Acylhydrazones
Author(s) -
Schneider Uwe,
Sugiura Masaharu,
Kobayashi Shū
Publication year - 2006
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.200505379
Subject(s) - chemistry , propargyl , nucleophile , base (topology) , catalysis , lewis acids and bases , dimethylformamide , organic chemistry , carbon fibers , combinatorial chemistry , solvent , composite number , composite material , mathematical analysis , mathematics , materials science
The highly selective preparation of various types of allenic and homopropargylic hydrazides through regiospecific allenylation and propargylation of the corresponding N ‐acylhydrazones is reported. These carbon‐carbon bond‐forming reactions employing in situ prepared propargyl‐ and allenyltrichlorosilanes proceed smoothly in N , N ‐dimethylformamide (DMF) without any metal catalysis (neutral Lewis base activation of nucleophiles). The use of Hünig's base as an additive is beneficial in terms of chemical yields.