Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes

Free radical initiated bicyclization of 1,6-enynes with chloralkanes, is achieved via selective activation of the C(sp3)-H bond of the chloralkane, resulting in diverse polychlorinated/chlorinated polyheterocycles. Two kinds of transformations and a scaled-up experiment were performed to test the synthetic importance of the organic chlorides. Finally, a range of radical inhibition operations and radical clock tests were explored to support the reaction process. A metal-free radical bicyclization of chloralkanes and 1,6-enynes produces various polychlorinated/chlorinated polyheterocycles.