01568nas a2200169 4500008004100000245009400041210006900135260000800204300001600212490000700228520094200235100002901177700002601206700002401232700002201256856012001278 2014 eng d00aTandem [4 + 2]/[2 + 2] cycloaddition reactions involving indene or benzofurans and arynes0 aTandem 4 22 2 cycloaddition reactions involving indene or benzof cJUN a3576–35790 v163 a

The reaction of arynes with indene/benzofurans has been developed. The arynes were generated from 2-(trimethylsilyl)aryl triflates by the fluoride-induced 1,2-elimination react with indene or various benzofurans proceeding via a cascade reaction involving the Diels–Alder reaction and a [2 + 2] cycloaddition reaction. The tandem process afforded functionalized dihydrobenzocyclobutaphenanthrenes in moderate to good yields. Moreover, the method has been utilized for the one-pot synthesis of benzo[b]fluoranthene.

1 aBhojgude, Sachin, Suresh1 aThangaraj, Manikandan1 aSuresh, Eringathodi1 aBiju, Akkattu, T. uhttps://library.ncl.res.in/content/tandem-4-22-2-cycloaddition-reactions-involving-indene-or-benzofurans-and-arynes01251nas a2200181 4500008004100000022001400041245012300055210006900178260007100247300001400318490000700332520049300339100002900832700003000861700002400891700002200915856013200937 2015 eng d a1523-706000aThree-component coupling involving arynes, aromatic tertiary amines, and aldehydes via aryl-aryl amino group migration0 aThreecomponent coupling involving arynes aromatic tertiary amine a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcDEC a6270-62730 v173 a

The transition-Metal-free multicomponent coupling of arynes, aromatic tertiary amines, and aldehydes proceeding via the aryl to aryl amino group migration has been demonstrated. This protocol allows rapid access to ortho-functionalized tertiary amines in moderate to good yields. Moreover, activated ketones can also be used as the aldehyde Component in the present reaction. The similarity of the aryl-aryl tertiary amino group migration with the Smiles rearrangement is striking.

1 aBhojgude, Sachin, Suresh1 aBaviskar, Dnyaneshwar, R.1 aGonnade, Rajesh, G.1 aBiju, Akkattu, T. uhttps://library.ncl.res.in/content/three-component-coupling-involving-arynes-aromatic-tertiary-amines-and-aldehydes-aryl-aryl-0