One‐Pot Oxidative Heteroannulations of N‐Sulfonylanilines with Styrenes for the Construction of 5‐Aminocoumaran Derivatives

Abstract

An efficient one-pot oxidative heteroannulation of N-sulfonylaniline derivatives with styrene derivatives for the rapid construction of 5-aminocoumaran derivatives is reported. Copper trifluoromethanesulfonate was found to be an excellent catalyst for the oxidative heteroannulation reactions with low reactive styrenes.

Metal‐Free Oxidative Carbon‐Heteroatom Bond Formation Through C–H Bond Functionalization

“…Similar hydroxylation of arenes was previously observed by Wang and co‐workers in the form of intermediates in the one‐pot oxidative heteroannulation of N ‐sulfonylanilines 117 with styrenes 118 to afford 5‐aminocoumaran derivatives 119 (Scheme ) 64. An N ‐sulfonylaniline in which the arene had no substituent at the para ‐position gave N ‐sulfonyl‐ p ‐aminophenol 120 on treatment with excess of PIFA in the presence of water.…”

Efficient Stereoselective Synthesis of Nitrocyclopropanes by the Oxidative Cyclization of Michael Adducts of Nitroolefins with Activated Methylene Compounds

“…As a part of our development of the synthetic applications of hypervalent iodine compounds, [15] we were delighted to find that the oxidative cyclopropanation of 1a occurred in the presence of PhIA C H T U N G T R E N N U N G (OAc) 2 and Bu 4 NBr, and afforded cyclopropane 2a in 51% yield with high diastereoselectivity after 12 h (Scheme 2).…”

Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents

“…In this "aromatic ring umpolung" process, PIDA oxidizes phenols to the corresponding phenoxenium ions, a very electrophilic species which reacts with various nucleophiles leading to the formation of diverse core structures prevalent in many natural products [87]. Along these lines, Fan and coworkers [88] documented an efficient one-pot PIFA-mediated oxidative heteroannulation of N-sulfonylaniline derivatives 116 with styrenes for the synthesis of 5-aminocoumaran derivatives 117 (Scheme 28 (3)).…”