Design principles of the use of alkynes in radical cascades

C Hu, J Mena, IV Alabugin - Nature Reviews Chemistry, 2023 - nature.com
One of the simplest organic functional groups, the alkyne, offers a broad canvas for the
design of cascade transformations in which up to three new bonds can be added to each of …

Radical cascade cyclization of 1, n-enynes and diynes for the synthesis of carbocycles and heterocycles

J Xuan, A Studer - Chemical Society Reviews, 2017 - pubs.rsc.org
Carbo-and heterocycles are widely found in natural products, biologically active structures,
medicinally relevant compounds, and in many other fine chemicals. The development of …

Radical cascades initiated by intermolecular radical addition to alkynes and related triple bond systems

U Wille - Chemical reviews, 2013 - ACS Publications
1. INTRODUCTION “Cascade” radical reactions, also known as “tandem” or “domino” radical
reactions, are characterized by the fact that they proceed through two or more consecutive …

Cyclizations of alkynes: revisiting Baldwin's rules for ring closure

K Gilmore, IV Alabugin - Chemical Reviews, 2011 - ACS Publications
According to the CRC dictionary of natural products, 1 90% of chemically individual
molecules discovered in nature contain either a carbocyclic or a heterocyclic subunit. 2 Not …

The Baldwin rules: revised and extended

K Gilmore, RK Mohamed… - Wiley Interdisciplinary …, 2016 - Wiley Online Library
The Baldwin rules constitute one of the clearest examples of the success which can be
obtained through the application of stereoelectronic concepts to reaction design. With …

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

MH Huang, WJ Hao, B Jiang - Chemistry–An Asian Journal, 2018 - Wiley Online Library
Over the past few years, the development of new radical reactions has gained considerable
momentum. Most such radical transformations heavily depend on the in situ generation of …

Concerted reactions that produce diradicals and zwitterions: electronic, steric, conformational, and kinetic control of cycloaromatization processes

RK Mohamed, PW Peterson, IV Alabugin - Chemical Reviews, 2013 - ACS Publications
The broad utility of cyclic structures accounts for the key roles that cycle-forming reactions
play in synthetic designs. Most of these reactions can be classified as either a cyclization of …

Finding the right path: Baldwin “Rules for Ring Closure” and stereoelectronic control of cyclizations

IV Alabugin, K Gilmore - Chemical Communications, 2013 - pubs.rsc.org
Truly important scientific breakthroughs often come from catching the glimpses of order in
chaos and distilling a large body of disjointed data into a clear set of simple concepts. Even …

Alkyne origami: folding oligoalkynes into polyaromatics

IV Alabugin, E Gonzalez-Rodriguez - Accounts of Chemical …, 2018 - ACS Publications
Conspectus Do not bend the triple bonds! This familiar undergraduate mantra must be
disobeyed if the alkyne group is used as a building block in molecular construction. This …

Selective transition state stabilization via hyperconjugative and conjugative assistance: stereoelectronic concept for copper-free click chemistry

B Gold, NE Shevchenko, N Bonus… - The Journal of …, 2012 - ACS Publications
Dissection of stereoelectronic effects in the transition states (TSs) for noncatalyzed azide–
alkyne cycloadditions suggests two approaches to selective transition state stabilization in …