Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers.

Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines†

Pd-catalyzed reaction of aryl halides and propargyl furylmethyl ethers: a novel pathway to functionalized dihydroisobenzofurans.

An interesting sequential reaction involving Sonogashira coupling, propargyl-allenyl isomerization, intramolecular [4 + 2] cycloaddition, and bridged oxa-ring opening has been realized, providing a facile method for the synthesis of functionalized dihydroisobenzofurans from easily accessible starting materials with a decent diastereoselectivity.

Gold(I)-catalyzed propargyl Claisen rearrangement.

Homoallenic alcohols are prepared from propargyl vinyl ethers using a trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4, as a catalyst for propargyl Claisen rearrangement at room temperature. The gold(I)-catalyzed reaction is effective for a diverse collection of propargyl vinyl ethers, including substrates containing aryl and alkyl groups at the propargylic position, and hydrogen, aryl, and alky...

Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides.

Pyrazino compounds such as quinoxalines are 1,4-diazines with widespread occurrence in nature. Quinolin-8-amines are isomerically related and valuable scaffolds in organic synthesis. Herein, we present intramolecular main group metal Lewis acid catalyzed formal hydroamination as well as hydroarylation methodology using mono-propargylated aromatic ortho-diamines. The annulations can be conducted...

Synthesis of the phenanthrene and cyclohepta[a]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes.

The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in...