Matches in SemOpenAlex for { <https://semopenalex.org/work/W2321507568> ?p ?o ?g. }
- W2321507568 endingPage "7140" @default.
- W2321507568 startingPage "7132" @default.
- W2321507568 abstract "Efficient bis(phosphine)nickel-catalyzed cross-couplings of diarylborinic acids with aryl chlorides, tosylates, and sulfamates have been effected with an assistance of N-heterocyclic carbene (NHC) generated in situ from N,N′-dialkylimidazoliums, e.g., N-butyl-N′-methylimidazolium bromide ([Bmim]Br), in toluene using K3PO4·3H2O as base. In contrast to bis(NHC)nickel-catalyzed conventional Suzuki coupling of arylboronic acids, mono(NHC)bis(phosphine)nickel species generated in situ from Ni(PPh3)2Cl2/[Bmim]Br displayed high catalytic activities in the cross-couplings of diarylborinic acids. The structural influences from diarylborinic acids were found to be rather small, while electronic factors from aryl chlorides, tosylates, and sulfamates affected the couplings remarkably. The couplings of electronically activated aryl chlorides, tosylates, and sulfamates could be efficiently effected with 1.5 mol % NiCl2(PPh3)2/[Bmim]Br as catalyst precursor to give the biaryl products in excellent yields, while 3–5 mol % loadings had to be used for the couplings of non- and deactivated ones. A small ortho-substitutent on the aromatic ring of aryl chlorides, tosylates, and sulfamates was tolerable. Applicability of the nickel-catalyzed cross-couplings in practical synthesis of fine chemicals has been demonstrated in process development for a third-generation topical retinoid, Adapalene." @default.
- W2321507568 created "2016-06-24" @default.
- W2321507568 creator A5020387219 @default.
- W2321507568 creator A5021653136 @default.
- W2321507568 creator A5047378133 @default.
- W2321507568 date "2014-07-23" @default.
- W2321507568 modified "2023-10-14" @default.
- W2321507568 title "N-Heterocyclic Carbene-Assisted, Bis(phosphine)nickel-Catalyzed Cross-Couplings of Diarylborinic Acids with Aryl Chlorides, Tosylates, and Sulfamates" @default.
- W2321507568 cites W1963833788 @default.
- W2321507568 cites W1963871974 @default.
- W2321507568 cites W1970979049 @default.
- W2321507568 cites W1977851260 @default.
- W2321507568 cites W1978890358 @default.
- W2321507568 cites W1981078281 @default.
- W2321507568 cites W1981876211 @default.
- W2321507568 cites W1982825189 @default.
- W2321507568 cites W1982874695 @default.
- W2321507568 cites W1986858488 @default.
- W2321507568 cites W1988742188 @default.
- W2321507568 cites W1992996188 @default.
- W2321507568 cites W1995168756 @default.
- W2321507568 cites W1999585247 @default.
- W2321507568 cites W2003432914 @default.
- W2321507568 cites W2003810621 @default.
- W2321507568 cites W2005712778 @default.
- W2321507568 cites W2007600985 @default.
- W2321507568 cites W2008491891 @default.
- W2321507568 cites W2009175466 @default.
- W2321507568 cites W2013048775 @default.
- W2321507568 cites W2013260769 @default.
- W2321507568 cites W2015780272 @default.
- W2321507568 cites W2016076296 @default.
- W2321507568 cites W2019161477 @default.
- W2321507568 cites W2020851876 @default.
- W2321507568 cites W2024323724 @default.
- W2321507568 cites W2026864887 @default.
- W2321507568 cites W2027369535 @default.
- W2321507568 cites W2027503474 @default.
- W2321507568 cites W2030786703 @default.
- W2321507568 cites W2032005375 @default.
- W2321507568 cites W2032731092 @default.
- W2321507568 cites W2033255996 @default.
- W2321507568 cites W2033467360 @default.
- W2321507568 cites W2034223040 @default.
- W2321507568 cites W2035515486 @default.
- W2321507568 cites W2038418968 @default.
- W2321507568 cites W2038639822 @default.
- W2321507568 cites W2043448287 @default.
- W2321507568 cites W2050023296 @default.
- W2321507568 cites W2050032539 @default.
- W2321507568 cites W2050442697 @default.
- W2321507568 cites W2063090974 @default.
- W2321507568 cites W2063815525 @default.
- W2321507568 cites W2063885683 @default.
- W2321507568 cites W2065561546 @default.
- W2321507568 cites W2066358035 @default.
- W2321507568 cites W2073341670 @default.
- W2321507568 cites W2075282171 @default.
- W2321507568 cites W2076941569 @default.
- W2321507568 cites W2079272184 @default.
- W2321507568 cites W2084910777 @default.
- W2321507568 cites W2093125996 @default.
- W2321507568 cites W2102784912 @default.
- W2321507568 cites W2105497471 @default.
- W2321507568 cites W2106446826 @default.
- W2321507568 cites W2110403492 @default.
- W2321507568 cites W2111545058 @default.
- W2321507568 cites W2112061711 @default.
- W2321507568 cites W2116558404 @default.
- W2321507568 cites W2122252398 @default.
- W2321507568 cites W2123591708 @default.
- W2321507568 cites W2131914170 @default.
- W2321507568 cites W2132236426 @default.
- W2321507568 cites W2138365237 @default.
- W2321507568 cites W2139232869 @default.
- W2321507568 cites W2141665100 @default.
- W2321507568 cites W2144603304 @default.
- W2321507568 cites W2144836181 @default.
- W2321507568 cites W2148396438 @default.
- W2321507568 cites W2152876843 @default.
- W2321507568 cites W2159724763 @default.
- W2321507568 cites W2165145376 @default.
- W2321507568 cites W2168315299 @default.
- W2321507568 cites W2169269629 @default.
- W2321507568 cites W2175081456 @default.
- W2321507568 cites W2290395892 @default.
- W2321507568 cites W2298119074 @default.
- W2321507568 cites W2313252583 @default.
- W2321507568 cites W2315752434 @default.
- W2321507568 cites W2317296363 @default.
- W2321507568 cites W2317645396 @default.
- W2321507568 cites W2319700679 @default.
- W2321507568 cites W2320199291 @default.
- W2321507568 cites W2322068719 @default.
- W2321507568 cites W2323585063 @default.
- W2321507568 cites W2330735882 @default.
- W2321507568 cites W2330888598 @default.
- W2321507568 cites W2331440625 @default.