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While progress has been made in their synthetic metholodology, the construction of \u03b2\u2010tertiary and C(sp<jats:sup>3<\/jats:sup>)\u2010rich <jats:italic>gem<\/jats:italic>\u2010diborylalkanes remains a synthetic challenge due to substrate limitations and steric hindrance issues. An approach is presented that utilizes synergistic photoredox and copper catalysis to achieve efficient C(sp<jats:sup>3<\/jats:sup>)\u2212C(sp<jats:sup>3<\/jats:sup>) cross\u2010coupling of alkyl <jats:italic>N<\/jats:italic>\u2010hydroxyphthalimide esters, which can easily be obtained from alkyl carboxylic acids, with diborylmethyl species, providing a series of C(sp<jats:sup>3<\/jats:sup>)\u2010rich <jats:italic>gem<\/jats:italic>\u2010diborylalkanes with 1\u00b0, 2\u00b0, and even 3\u00b0 \u03b2 positions. 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