Small Molecule Activation with Intramolecular “Inverse” Frustrated Lewis Pairs

Manankandayalage, Chamila; Unruh, Daniel K.; Krempner, Clemens

doi:10.1002/chem.202005143

Title: Small Molecule Activation with Intramolecular “Inverse” Frustrated Lewis Pairs

Journal Article · Wed Feb 10 00:00:00 EST 2021 · Chemistry - A European Journal

DOI:https://doi.org/10.1002/chem.202005143· OSTI ID:1775423

Manankandayalage, Chamila ^[1]; Unruh, Daniel K. ^[1];

^[1]

Texas Tech Univ., Lubbock, TX (United States)

Abstract The intramolecular “inverse” frustrated Lewis pairs (FLPs) of general formula 1‐BR ₂ ‐2‐[(Me ₂ N) ₂ C=N]‐C ₆ H ₄ ( 3 – 6 ) [BR ₂ =BMes ₂ ( 3 ), BC ₁₂ H ₈ , ( 4 ), BBN ( 5 ), BBNO ( 6 )] were synthesized and structurally characterized by multinuclear NMR spectroscopy and X‐ray analysis. These novel types of pre‐organized FLPs, featuring strongly basic guanidino units rigidly linked to weakly Lewis acidic boryl moieties via an ortho ‐phenylene linker, are capable of activating H−H, C−H, N−H, O−H, Si−H, B−H and C=O bonds. 4 and 5 deprotonated terminal alkynes and acetylene to form the zwitterionic borates 1‐(RC≡C‐BR ₂ )‐2‐[(Me ₂ N) ₂ C=NH]‐C ₆ H ₄ (R=Ph, H) and reacted with ammonia, BnNH ₂ and pyrrolidine, to generate the FLP adducts 1‐(R ₂ HN→BR ₂ )‐2‐[(Me ₂ N) ₂ C=NH]‐C ₆ H ₄ , where the N‐H functionality is activated by intramolecular H‐bond interactions. In addition, 5 was found to rapidly add across the double bond of H ₂ CO, PhCHO and PhNCO to form cyclic zwitterionic guanidinium borates in excellent yields. Likewise, 5 is capable of cleaving H ₂ , HBPin and PhSiH ₃ to form various amino boranes. Collectively, the results demonstrate that these new types of intramolecular FLPs featuring weakly Lewis acidic boryl and strongly basic guanidino moieties are as potent as conventional intramolecular FLPs with strongly Lewis acidic units in activating small molecules.

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Research Organization:: Texas Tech Univ., Lubbock, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF); USDOE

Grant/Contract Number:: SC0019094; 1407681

OSTI ID:: 1775423

Alternate ID(s):: OSTI ID: 1781959

Journal Information:: Chemistry - A European Journal, Vol. 27, Issue 20; ISSN 0947-6539

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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08 HYDROGEN
36 MATERIALS SCIENCE
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Small molecule activation
Hydrogen cleavage
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Title: Small Molecule Activation with Intramolecular “Inverse” Frustrated Lewis Pairs

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