Alkenes as alkyne equivalents in radical cascades terminated by fragmentations: overcoming stereoelectronic restrictions on ring expansions for the preparation of …

RK Mohamed, S Mondal, B Gold… - Journal of the …, 2015 - ACS Publications
… To gain further insight into the relative reactivity of disubstituted alkynes and alkenes toward
Bu 3 Sn radicals, we performed competition experiments in which an equimolar mixture of …

Design principles of the use of alkynes in radical cascades

C Hu, J Mena, IV Alabugin - Nature Reviews Chemistry, 2023 - nature.com
… polyaromatics than their endo-dig counterparts. For the all-exo … fragmentations that restore
the alkyne moiety. If the same … , it is used for selective termination of radical cascades. We will …

Design of Leaving Groups in Radical C C Fragmentations: Through‐Bond 2c–3e Interactions in Self‐Terminating Radical Cascades

S Mondal, B Gold, RK Mohamed… - Chemistry–A European …, 2014 - Wiley Online Library
… We have described a radical cascade that self-terminates by expulsion of primary C-…
into self-terminating radical cascades allows the use of alkenes as alkyne equivalents for the …

Programming organic molecules: Design and management of organic syntheses through free‐radical cascade processes

AJ McCarroll, JC Walton - Angewandte Chemie International …, 2001 - Wiley Online Library
… If an intermediate radical cleaves into two or more fragments … Acyl radical equivalents, derived
from vinyl radicals, have … rather than a silylated alkyne) the ketyl radical was generated by …

Alkyne origami: folding oligoalkynes into polyaromatics

IV Alabugin, E Gonzalez-Rodriguez - Accounts of Chemical …, 2018 - ACS Publications
… how alkenes can be used as alkyne equivalents in cyclizations coupled with fragmentations
… In summary, the first part of this Account described the evolution of radical all-exo cascades: …

Alkynes as synthetic equivalents of ketones and aldehydes: a hidden entry into carbonyl chemistry

IV Alabugin, E Gonzalez-Rodriguez, RK Kawade… - Molecules, 2019 - mdpi.com
… will show a cascade transformation of an alkyne that involves … cross-coupling and
fragmentation presented in this work … weakened by the oxyanionic radical stabilizing groups. This …

… with C–C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals

CJ Evoniuk, GP Gomes, M Ly, FD White… - The Journal of …, 2017 - ACS Publications
alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics.
This method utilizes alkenes as synthetic equivalents of alkynescascade terminated by C…

Organic syntheses through free-radical annulations and related cascade sequences

AJ McCarroll, JC Walton - Journal of the Chemical Society, Perkin …, 2001 - pubs.rsc.org
alkynes and alkenes have been shown to be suitable radical … by a rapid dissociative
fragmentation, with which intermolecular … radical was sufficiently rapid to allow 22 equivalents of …

The Missing C1–C5 Cycloaromatization Reaction: Triplet State Antiaromaticity Relief and Self-Terminating Photorelease of Formaldehyde for Synthesis of Fulvenes …

RK Mohamed, S Mondal, K Jorner… - Journal of the …, 2015 - ACS Publications
… the use of alkenes as alkyne equivalents in … alkene terminus can facilitate the C–C
fragmentation, but a facile intramolecular path for the final H-abstraction at the exocyclic vinyl radical

Coupling cyclizations with fragmentations for the preparation of heteroaromatics: quinolines from o-alkenyl arylisocyanides and boronic acids

CJ Evoniuk, M Ly, IV Alabugin - Chemical Communications, 2015 - pubs.rsc.org
equivalents of alkynes in reaction cascades that are terminated by C–C bond fragmentation.
… OMe groups can facilitate the desired radical fragmentation pathway, we focused our efforts …