The use of ( L )Ni( o -tolyl)Cl precatalysts ( L = PAd-DalPhos or CyPAd-DalPhos) enables the C( sp 2 )–O cross-coupling of primary, secondary, or tertiary aliphatic alcohols with (hetero)aryl electrophiles, including unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In addition to offering a competitive alternative to palladium catalysis, this work establishes the feasibility of utilizing ancillary ligation as a complementary means of promoting challenging nickel-catalyzed C( sp 2 )–O cross-couplings, without recourse to precious-metal photoredox catalytic methods.
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MacQueen et al. (2018) studied this question.
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