A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes

Abstract

A direct and practical approach for the construction of DBTs was developed via a Pd-catalyzed tandem reaction, in which commercially available o-bromo-iodobenzenes combined with benzene thiols or iodobenzenes combined with o-bromo-benzene thiols were applied.

Recent Advances in the Synthesis of Dibenzothiophenes

“…In 2018, Song and coworkers [20] designed a simple and practical Pd-catalyzed tandem reaction to construct dibenzothiophene (Scheme 11). The reaction was conducted through one-step synthesis employing commercially available o-bromoiodobenzene and benzenethiol or benzenethiol and o-bromo-benzenethiol as precursor materials to synthesize a series of dibenzothiophenes and their derivatives.…”

Facile Synthesis of Thienoacenes via Transition-Metal-Free Ladderization

“…Although dibenzo­[ b , d ]­thiophene ( 2a ), the basic structural unit of the BTA systems, is a well-known compound that can be easily obtained from various precursors, − only a few ladderization methods are suitable for the synthesis of extended BTA systems.…”

Bromothiolation of Arynes for the Synthesis of 2-Bromobenzenethiol Equivalents

“…A wide variety of molecules having organosulfur skeletons such as phenothiazine, thianthrene, thienothiophene, and so on play pivotal roles in broad research fields (Figure A) . A number of methods to construct these significant organosulfur skeletons from o -bromobenzenethiols have been developed by virtue of good reactivities of thiol and bromide moieties . However, it is not easy to prepare diverse o -bromobenzenethiols from the corresponding anilines by conventional methods due to the regioselectivity in ortho -bromination of the amino group and poor functional group tolerance in the following diazotization–thiolation through highly reactive diazonium intermediates (Figure B) .…”

“… 1 A number of methods to construct these significant organosulfur skeletons from o -bromobenzenethiols have been developed by virtue of good reactivities of thiol and bromide moieties. 2 However, it is not easy to prepare diverse o -bromobenzenethiols from the corresponding anilines by conventional methods due to the regioselectivity in ortho -bromination of the amino group and poor functional group tolerance in the following diazotization–thiolation through highly reactive diazonium intermediates ( Figure 1 B). 3 In addition, high oxidizability under air as well as the bad smell of o -bromobenzenethiols makes the synthesis of highly functionalized derivatives difficult.…”