NDLI: Z-Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters† †Electronic supplementary information (ESI) available: Full procedures, computational details and characterization data. See DOI: 10.1039/c7sc04283c

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Z-Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters† †Electronic supplementary information (ESI) available: Full procedures, computational details and characterization data. See DOI: 10.1039/c7sc04283c

Content Provider	Semantic Scholar
Author	Thomas, Bryce N. Moon, Patrick J. Yin, Shengkang Brown, Alex Lundgren, Rylan J.
Copyright Year	2018
Abstract	A well-defined Ir-allyl complex catalyzes the Z-selective cross-coupling of allyl carbonates with α-aryl diazo esters. The process overrides the large thermodynamic preference for E-products typically observed in metal-mediated coupling reactions to enable the synthesis of Z,E-dieneoates in good yield with selectivities consistently approaching or greater than 90 : 10. This transformation represents the first productive merger of Ir-carbene and Ir-allyl species, which are commonly encountered intermediates in allylation and cyclopropanation/E-H insertion catalysis. Potentially reactive functional groups (aryl halides, ketones, nitriles, olefins, amines) are tolerated owing to the mildness of reaction conditions. Kinetic analysis of the reaction suggests oxidative addition of the allyl carbonate to an Ir-species is rate-determining. Mechanistic studies uncovered a pathway for catalyst activation mediated by NEt3.
Starting Page	238
Ending Page	244
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1039/c7sc04283c
PubMed reference number	29629093
Journal	Medline
Volume Number	9
Alternate Webpage(s)	http://pubs.rsc.org/en/content/articlepdf/2018/sc/c7sc04283c
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/sc/c7sc04283c/c7sc04283c1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c7sc04283c
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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