Three
types of novel radical cyclization of 1,6-enynes with sulfonyl
hydrazides have been presented, which provided convenient synthetic
approaches for accessing five-membered cyclic lactams, five-membered
cyclic lactams containing C–I bond, and six-membered cyclic
lactams. Notably, these transformations are implemented in metal-catalyst-free
systems, in which three classes of important lactam derivatives were
synthesized with selectivity and controllability from the same substrate
using water as the green solvent.
The construction of all-carbon quaternary centers, especially those containing an alkyne-substituted framework, represents an important challenge in organic synthesis. Here we present a novel Fe-catalyzed selective formal insertion of diazo compounds into C(sp)−C(sp 3 ) bonds of propargyl alcohols under mild conditions that enables the streamlined construction of alkynesubstituted all-carbon quaternary centers. This unique strategy starts with in situ generation of an ester group in the presence of carboxylic acids, followed by insertion of metal-carbene into C(sp)− C(sp 3 ) bonds, which may open up a new reaction mode for exploring metal-carbene insertion into acyclic C−C bonds.
A novel 5-exo-dig/6-endo-trig bicyclization of 1,6-enynes with sulfonyl hydrazides in aqueous phase using cheap and available tetrabutylammonium iodide (TBAI)-tert-butyl hydroperoxide (TBHP) combined system is reported. The resulting reaction of diverse...
We describe a method for radical cyclization of N-methacryloyl-2-arylbenzoimidazoles with nitriles, ketones, and tert-butyl nitrite (TBN) for the preparation of benzimidazo[2,1-a]isoquinolin-6(5H)-ones with the advantage of mild reaction conditions, excellent functional group compatibility and broad substrate scope. The present strategy has favorable characteristics: (1) the use of cheap metal catalysis; (2) N-radical initiated cyclization of N-methacryloyl-2-arylbenzoimidazoles; (3) rare example of radical C(sp3)–H functionalization in this cyclization.
A novel polychloromethylation/acyloxylation of 1,6-enynes with chloroalkanes and diacyl peroxides through dual roles designs to prepare 2-pyrrolidinone derivatives with polychloromethyl units has been developed by the use of inexpensive copper...
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