Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• (indolyl)methane compounds were isolated in moderate and excellent yields after 24 hours in DMSO, Et3N and formic acid as additives and, Pd(PPh3)2Cl2/P(o-tolyl)3 as catalyst system. The reaction conditions and some important BIMs synthesized are shown in Scheme 42. In the second paper they used

• -3-yl aryl ketones reported by Zhao and co-workers [73] (path a) and Zhang and co-workers [74] (path b). Pd-catalyzed carbonylative synthesis of BIMs from aryl iodides and N-substituted and NH-free indoles with of TFBen as CO source. Cu-catalyzed direct double-carbonylation and monocarbonylation of

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• (indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti

• -inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness of our society, the focus has shifted towards the

• development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• ), CSIC-Universidad de Zaragoza. E-50009 Zaragoza, Spain 10.3762/bjoc.10.228 Abstract A novel approach for the catalyzed formation of bisindolylmethane derivatives (BIMs) is described. This methodology is the unique example where AgOTf has been successfully used for the activation of aldehydes, giving

• bisindolylmethane derivatives (BIMs), many of them isolated from marine natural sources [15][16] and are an important class of indole derivatives which exhibit an appealing range of biological properties such as antibacterial, antifungal, antimicrobial or anti-inflammatory, among others (Figure 1) [17

• ]. Interestingly, BIMs have also been found to be potent anticancer derivatives, also having antimetastatic activity, and clinical studies have demonstrated that they could be potentially used as chemotherapeutic agents against numerous forms of cancer [18][19][20]. The great importance of bisindolylmethanes, has