Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration

Zhang, Guoqi; Wu, Jing; Zeng, Haisu; Neary, Michelle C.; Devany, Matthew; Zheng, Shengping; Dub, Pavel A.

doi:10.1021/acscatal.8b04096

Title: Dearomatization and Functionalization of Terpyridine Ligands Leading to Unprecedented Zwitterionic Meisenheimer Aluminum Complexes and Their Use in Catalytic Hydroboration

Journal Article · 31 December 2018 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.8b04096 · OSTI ID:1492666

^[1]; Wu, Jing ^[2]; Zeng, Haisu ^[2];

^[3]; Devany, Matthew ^[3]; Zheng, Shengping ^[3];

^[4]

City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College
City Univ. (CUNY), NY (United States). Graduate Center, Dept. of Sciences, John Jay College; City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
City Univ. (CUNY), NY (United States). Hunter College, Dept. of Chemistry
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Here, this paper reports the first example of dearomatization of ubiquitous terpyridine (tpy) ligands via 2'/6'-, 3'/5'-, or 4'-selective alkylation of the central pyridine ring. The reaction is mediated by the most abundant metal in the Earth’s crust, aluminum (Al), and depending on the conditions employed, exhibits ionic or radical character as suggested by experimental and computational analysis. In the latter case, intermediate formation of an AlIII complex supported by π-radical monoanionic ligand (tpy•)^1– is apparent. The 3'/5'-alkylation leads to unprecedented zwitterionic Meisenheimer Al^III complexes, which were identified as efficient precatalysts for the selective hydroboration of C=O and C≡C functionalities. Turnover numbers (TONs) up to ~1000 place the corresponding complexes in the category of the most efficient Al catalysts reported to date for the title reaction. The acquired data suggest that aluminum monohydrides, or more likely dihydrides, could be relevant catalytic species. Alternatively, one can also imagine a mechanistic scenario in which the dearomatized “chemically noninnocent” ligand acts as hydride donor, and a detailed investigation of this is warranted in the future.

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Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: National Science Foundation (NSF); John Jay College; USDOE

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 1492666

Report Number(s):: LA-UR-18-24664

Journal Information:: ACS Catalysis, Vol. 9; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 59 works

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Inorganic and Physical Chemistry
Organic Chemistry

CCDC 1833908: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkbb6 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833909: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkbc7 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833910: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkbd8 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833911: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkbf9 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1834247: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkp8h The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833905: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkb73 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833906: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkb84 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1833907: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1zkb95 The current record is supplemented by this dataset	dataset	January 2019
CCDC 1585884: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1q77kr The current record is supplemented by this dataset	dataset	January 2019
CCDC 1585885: Experimental Crystal Structure Determination Guoqi, Zhang,; Jing, Wu,; Haisu, Zeng, https://doi.org/10.5517/ccdc.csd.cc1q77ls The current record is supplemented by this dataset	dataset	January 2019