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US 10,370,393 B2Granted
Stereoretentive cross-coupling of boronic acids
AssigneeThe Board of Trustees of the University of Illinois
InventorsMartin D. Burke, Ian Crouch, Jonathan Lehmann, Andrea Palazzolo, Claire Simons
Life of this patent
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Abstract
The present disclosure provides tri-orthoalkylphenyl phosphine catalysts of formula I wherein A is CH2, C═O, or NRA; R1 is aryl, heteroaryl, isopropyl, tert-butyl, cycloalkyl, or heterocycloalkyl, wherein aryl, heteroaryl, cycloalkyl and heterocycloalkyl are optionally substituted; R2 is H, (C1-C8)alkyl, (C1-C8)alkoxy, N(RA)2, or an electron withdrawing group; and each RA is independently H or (C1-C8)alkyl; that are tuned electrically and sterically.
Claims7
A phosphine compound of Formula I:
- wherein
- A is CH2, C═O, or NRA;
- R1 is aryl, heteroaryl, tert-butyl, cycloalkyl, or heterocycloalkyl, wherein aryl, heteroaryl, cycloalkyl and heterocycloalkyl are optionally substituted;
- R2 is H, (C1-C8)alkyl, (C1-C8)alkoxy, N(RA)2, or an electron withdrawing group;
- and
- each RA is independently H or (C1-C8)alkyl;
- wherein the electron withdrawing group is halo, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, nitrile, nitro, CO2RA, C(O)N(RA)2, SO2RA, SO2N(RA)2, or P(O)[N(RA)2]2.
4 more elements
A The phosphine compound of Formula II:
- wherein
- R1 is phenyl or (C3-C6)cycloalkyl, wherein phenyl and (C3-C6)cycloalkyl are optionally monosubstituted or disubstituted;
- and
- R2 is H, (C1-C5)alkyl, (C1-C5)alkoxy, N(RA)2, halo, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, nitrile, nitro, CO2RA, or C(O)N(RA)2;
- and each RA is independently H or (C1-C8)alkyl.
2 more elements
Dependencies are inferred from the claim text.