Cyclic (Alkyl)(amino)carbenes: Synthesis of Iminium Precursors and Structural Properties

Vermersch, François; Oliveira, Luana; Hunter, Joseph; Soleilhavoup, Michele; Jazzar, Rodolphe; Bertrand, Guy

doi:10.1021/acs.joc.1c03075

Cyclic (Alkyl)(amino)carbenes: Synthesis of Iminium Precursors and Structural Properties

Journal Article · Mon Feb 07 23:00:00 EST 2022 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/acs.joc.1c03075· OSTI ID:1905846

^[1]; Oliveira, Luana ^[2]; Hunter, Joseph ^[2]; ^[2]; ^[2]; ^[2]

Univ. of California, San Diego, CA (United States). UCSD-CNRS Joint Research Lab.; UCSD
Univ. of California, San Diego, CA (United States). UCSD-CNRS Joint Research Lab.

Using readily available pre-allylated aldehydes, in this work we report a simple and divergent synthesis of cyclic (alkyl)(amino)carbene (CAAC) iminium precursors. Using a combination of crystallographic data and steric maps, we further elaborate on the specific steric properties of CAAC ligands with respect to state-of-the-art phosphine and carbene ligands.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, San Diego, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); French National Research Agency (ANR)

Grant/Contract Number:: SC0009376

OSTI ID:: 1905846

Journal Information:: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 5 Vol. 87; ISSN 0022-3263

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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CCDC 2127092: Experimental Crystal Structure Determination François, Vermersch,; Luana, Oliveira,; Joseph, Hunter, https://doi.org/10.5517/ccdc.csd.cc29ddw0 The current record is supplemented by this dataset	dataset	January 2022
CCDC 2127093: Experimental Crystal Structure Determination François, Vermersch,; Luana, Oliveira,; Joseph, Hunter, https://doi.org/10.5517/ccdc.csd.cc29ddx1 The current record is supplemented by this dataset	dataset	January 2022
CCDC 2127094: Experimental Crystal Structure Determination François, Vermersch,; Luana, Oliveira,; Joseph, Hunter, https://doi.org/10.5517/ccdc.csd.cc29ddy2 The current record is supplemented by this dataset	dataset	January 2022
CCDC 2127095: Experimental Crystal Structure Determination François, Vermersch,; Luana, Oliveira,; Joseph, Hunter, https://doi.org/10.5517/ccdc.csd.cc29ddz3 The current record is supplemented by this dataset	dataset	January 2022
CCDC 2127096: Experimental Crystal Structure Determination François, Vermersch,; Luana, Oliveira,; Joseph, Hunter, https://doi.org/10.5517/ccdc.csd.cc29df05 The current record is supplemented by this dataset	dataset	January 2022
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Cyclic (Alkyl)(amino)carbenes: Synthesis of Iminium Precursors and Structural Properties

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