Premium
Synthesis of C4‐Acyl Glycosides by Cross‐Ketonization: The Importance of Precise Temperature Control in Photochemistry
Author(s) -
Lacker Caitlin R.,
Neumann Max,
Abrams Dylan J.,
Martinelli Joseph R.,
Stahl Shan S.,
Yoon Tehshik P.
Publication year - 2025
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202501408
Subject(s) - decarboxylation , chemistry , catalysis , yield (engineering) , glycoside , quantum yield , reaction mechanism , reaction rate , photochemistry , organic chemistry , combinatorial chemistry , thermodynamics , fluorescence , physics , quantum mechanics
Abstract We describe herein a method for the synthesis of reversed C ‐acyl glycosides by direct cross‐ketonization of linear carboxylic acids with carboxy sugars under metallaphotoredox conditions. This reaction proves to be highly sensitive to reaction temperature, with the reproducibility and yield of ketonization highly dependent upon precise temperature control. Analysis of the reaction mechanism suggests this sensitivity reflects the need to match the rate of Ni catalytic turnover with the rate of photocatalytic decarboxylation of the carboxy sugar. The insights gained from this study have important implications for the study of all metallaphotoredox reactions as well as other photoreactions that involve dual catalytic cycles.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom