TY - JOUR
T1 - Catalytic rearrangements of onium ylides in aromatic systems
AU - Nair, Vaishnavi N.
AU - Tambar, Uttam K.
N1 - Funding Information:
Financial support was provided by W. W. Caruth, Jr. Endowed Scholarship, Welch Foundation (I-1748), National Institutes of Health (R01GM102604), American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and Sloan Research Fellowship. V. N. N. acknowledges the Sarah and Frank McKnight Fund Graduate Fellowship. We also thank our diverse collection of lab members for creating a supportive environment for research.
Publisher Copyright:
© 2022 The Royal Society of Chemistry
PY - 2022/3/25
Y1 - 2022/3/25
N2 - Onium ylides are reactive intermediates that undergo versatile chemical transformations to give structurally interesting compounds. Rearrangement reactions of onium ylides are of great importance to synthetic organic chemists, as they provide efficient methods for C-C bond formations as well as installation of new stereogenic centers in molecules. Traditionally, onium ylides have been shown to undergo two types of rearrangements, namely, [2,3]- and [1,2]-rearrangements. In recent years, there have been tremendous developments in the field of metal-catalyzed onium ylide rearrangements through catalytic generation of ylide intermediates from diazocompounds. Several examples of selective catalytic onium ylide rearrangements involving sulfonium, oxonium, ammonium, as well as iodonium ylides have been developed over the years especially in allylic and propargylic systems. However, when the π-system that takes part in the rearrangement is part of an aromatic ring, the selectivity for rearrangements of reactive onium ylides is more challenging. In this review, we discuss recent advances in catalyst control of onium ylide rearrangements of aromatic systems.
AB - Onium ylides are reactive intermediates that undergo versatile chemical transformations to give structurally interesting compounds. Rearrangement reactions of onium ylides are of great importance to synthetic organic chemists, as they provide efficient methods for C-C bond formations as well as installation of new stereogenic centers in molecules. Traditionally, onium ylides have been shown to undergo two types of rearrangements, namely, [2,3]- and [1,2]-rearrangements. In recent years, there have been tremendous developments in the field of metal-catalyzed onium ylide rearrangements through catalytic generation of ylide intermediates from diazocompounds. Several examples of selective catalytic onium ylide rearrangements involving sulfonium, oxonium, ammonium, as well as iodonium ylides have been developed over the years especially in allylic and propargylic systems. However, when the π-system that takes part in the rearrangement is part of an aromatic ring, the selectivity for rearrangements of reactive onium ylides is more challenging. In this review, we discuss recent advances in catalyst control of onium ylide rearrangements of aromatic systems.
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U2 - 10.1039/d2ob00218c
DO - 10.1039/d2ob00218c
M3 - Review article
C2 - 35388871
AN - SCOPUS:85129317296
SN - 1477-0520
VL - 20
SP - 3427
EP - 3439
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 17
ER -