Group 13 exchange and transborylation in catalysis

• Dominic R. Willcox and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28

• functionalisation of unsaturated bonds [1][2][3][4][5], and, more recently, frustrated Lewis pair (FLP) chemistries including small molecule activations and C–H insertion reactions [6][7][8][9][10]. Group 13 exchange is the transfer of one or more substituents from one group 13 element to another group 13 element

• frustrated Lewis pair (FLP)-mediated C‒H functionalisation (Scheme 4a). Using computational analysis, the mechanism of the reaction was proposed to occur by borane dimer [9]2 dissociation, followed by a concerted deprotonation of the heterocycle 10 to give a zwitterionic intermediate 11. The zwitterion then

Catalyzed and uncatalyzed procedures for the syntheses of isomeric covalent multi-indolyl hetero non-metallides: an account

• Ranadeep Talukdar

Beilstein J. Org. Chem. 2021, 17, 2102–2122, doi:10.3762/bjoc.17.137

• similar mechanism (Scheme 8b) [62][63]. The reduced form of indole, i.e., indoline 50 coordinates with the Lewis acid to form a complex which activates PhSiH3 (frustrated Lewis pair) for silylation (69, Scheme 8b). Phosphines The base-mediated syntheses of bis(indol-2-yl)phosphines 76 and 78 were

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• ] cycloadditions [109][110] or polymeric products [6][71][109][118], which are often not desired due to the difficulties associated with purification. Additionally, a formal [6 + 4] dimerization was reported by Mömming et al. utilising frustrated Lewis pair chemistry (Scheme 9), however, the mechanism of this

• transition state is shown as the intermediate [4]. Dimerization of pentafulvenes via a Diels–Alder cycloaddition pathway whereby one fulvene acts as a diene and the second fulvene acts as a dienophile. Dimerization of pentafulvenes via frustrated Lewis pair chemistry as reported by Mömming et al. [116

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

• Sem Raj Tamang and
• James D. Hoefelmeyer

Beilstein J. Org. Chem. 2016, 12, 2757–2762, doi:10.3762/bjoc.12.272

• use of ambiphilic molecules as ligands for transition metals has given rise to an important new class of catalysts [49]. In previous work from our laboratory, we prepared the intramolecular frustrated Lewis pair 8-quinolyldimesitylborane (1) and its complexes with Cu(I), Ag(I), and Pd(II) [50

Metal–ligand multiple bonds as frustrated Lewis pairs for C–H functionalization

• Matthew T. Whited

Beilstein J. Org. Chem. 2012, 8, 1554–1563, doi:10.3762/bjoc.8.177

• demonstrate that the resultant reactivity may be a powerful tool for the functionalization of C–H and E–H bonds. Keywords: ambiphilic reactivity; C–H activation; C–H functionalization; frustrated Lewis pair; metal carbene; multiple bond; Introduction Orbital cooperation has long been recognized as an