New reagents have been sought for directed $ortho$ cupration in which the use of cyanide reagents is eliminated. CuOCN reacts with excess TMPLi (TMP = 2,2,6,6-tetramethylpiperidide) in the presence of limited donor solvent to give crystals that are best represented as (TMP)$2$Cu$\mathrm{<mrow\; data-mjx-texclass="ORD">0.1</mrow>}$Li$\mathrm{<mrow\; data-mjx-texclass="ORD">0.9</mrow>}$(OCN)Li$2$(THF) 8, whereby both Lipshutz-type lithiocuprate (TMP)$2$Cu(OCN)Li$2$(THF) 8a and trinuclear (TMP)$2$(OCN)Li$3$(THF) 8b are expressed. Treatment of a hydrocarbon solution of TMP$2$CuLi 9a with LiOCN and THF gives pure 8a. Meanwhile, formation of 8b is systematized by reacting (TMPH$2$)OCN 10 with TMPH and $n$BuLi to give (TMP)$2$(OCN)Li$3$(THF)$2$ 11. Important to the attribution of lower/higher order bonding in lithiocuprate chemistry is the observation that in crystalline 8, amide-bridging Cu and Li demonstrate clear preferences for di- and tricoordination, respectively. A large excess of Lewis base gives an 8-membered metallacycle that retains metal disorder and analyses as (TMP)$2$Cu$\mathrm{<mrow\; data-mjx-texclass="ORD">1.35</mrow>}$Li$\mathrm{<mrow\; data-mjx-texclass="ORD">0.65</mrow>}$ 9 in the solid state. NMR spectroscopy identifies 9 as a mixture of (TMP)$2$CuLi 9a and other copper-rich species. Crystals from which the structure of 8 was obtained dissolve to yield evidence for 8b coexisting in solution with $in\; situ$-generated 9a, 11 and a kinetic variant on 9a ($i$-9a), that is best viewed as an agglomerate of TMPLi and TMPCu. Moving to the use of DALi (DA = diisopropylamide), (DA)$2$Cu$\mathrm{<mrow\; data-mjx-texclass="ORD">0.09</mrow>}$Li$\mathrm{<mrow\; data-mjx-texclass="ORD">0.91</mrow>}$(Br)Li$2$(TMEDA)$2$ 12 (TMEDA = $N$,$N$,$N\prime$,$N\prime$ -tetremethylethylenediamine) is isolated, wherein (DA)$2$Cu(Br)Li$2$(TMEDA)$2$ 12a exhibits lower-order Cu coordination. The preparation of (DA)$2$Li(Br)Li$2$(TMEDA)$2$ 12b was systematized using (DAH$2$)Br, DAH and $n$BuLi. Lastly, metal disorder is avoided in the 2 : 1 lithium amide : Lipshutztype monomer adduct (DA)$4$Cu(OCN)Li$4$(TMEDA)$2$ 13.