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022, 12, x FOR PEER REVIEW 2 of 8 Crystals 2022, 12, 1339 replacing toxic cyanide to form the initial C-B bond (Scheme 1B) [20]. Later, the group of Kennedy used formaldehyde and decaborane to form the B-C bond, which could simplify the synthetic route and save the trouble of a C-N bond fracture (Scheme 1C) [21]. How- 2 of 7 which could simplify the synthetic route and save the trouble of a C-N bond fracture ever, the conditions for closing the cage by adding Me2S·BH3 require harsh reaction con- (Scheme 1C) [21]. However, the conditions for closing the cage by adding Me2S·BH3 ditions such as 3 days of heating. require harsh reaction conditions such as 3 days of heating. H 9HH6H8H H105H I 9 117 II 10 87 43 432 562 1 I 1 Me3N+ I H 1 456 32 path B (1) RCN (2) NaOH, Me2SO4 H (1) BH3.NEt3, 180 oC (2) Me2SO4, OH- H (3) Na, NH3 H H H H 1 2 II I 7 HH 12 2 9 10 8 11 HH II CF3SiMe3 2 II HH NaH path E Scheme 1. SynStchheesmiseo1f.[SMyne3tNheHsi]s[oCfB[1M1He31N2]Hfr]o[CmBB111H0H121]4 f(rAo–mCB)1a0nHd14[M(Ae–3CN)Han][dB[1M1He134N] (HD][–BF1)1.H14] (D–F). To avoid the use of toxic decaborane, the [B H ]− anion was introduced to the − 1114 To avoid the use of toxic decaborane, the [B11H14] anion was introduced to the syn- synthesis of [CB11H12]− [22–25]. In 2001, Michl’s group reported a relatively safe way thesis of [CB11H12]− [22–25]. In 2001, Michl’s group reported a relatively safe way to syn- to synthesize [CB11H12]− by deprotonation of [B11H14]−, followed by the insertion of thesize [CB11H12]− by deprotonation of [B11H14]−, followed by the insertion of dichlorocar- dichlorocarbene, but the yield was very low due to the low activity of the selected car- bene, but the yield was very low due to the low activity of the selected carbene source bene source (Scheme 1D). Agnes Kütt and co-workers found that [Me3NH][CB11H12] (Scheme 1D). Agnes Kütt and co-workers found th−at [Me3NH][CB11H12] could be obtained could be obtained by reacting [B11H14] with NaH and CF3SiMe3 in up to 95% yield −− by reacting [(BS1c1hHe1m4]ew1Eit)h[2N4a].HBaynidmCprFo3vSinMget3hienaubpovtoe 9m5e%thyodie,ld[C(BSchHem]e 1wEa)s[2s4y]n.tBhyesimze-d with − proving the acboomvmeomneltahbodra,t[oCryB1r1eHag12e]nwtsassucshynatshNesaiOzeHd, KwiCthOcoamndmConHClalb,odraetsoprityertehaegyeineltds being 233 relatively low (40%) (Scheme 1F) [25]. Obviously, recent studies mainly focused on the such as NaOH, K2CO3 and CHCl3, despite the yield being relatively low (40%) (Scheme synthesis for the [Me NH]+ salt of [CB H ]−, while methods on the direc+t synthesis 1F) [25]. Obviously, recent studie3s mainly focused11on12the synthesis for the [Me3NH] salt of alkali metal (M = Na, K) salts of the [CB H ]− anion are still very limited, which is − 11 12 of [CB11H12] , while methods on the direct synthesis of alkali metal (M = Na, K) salts of the − inconsistent with the great application of alkali metal (M = Na, K) salts of the [CB11H12]− [CB11H12] anion are still very limited, which is inconsistent with the great application of anion. Recently, we improved the synthetic method of [Et4N][closo-1-CHB9H9] [26], and alkali metal (M = Na, K) salts of the [CB11H12]− anion. Recently, we improved the synthetic on the basis of our previous work on the condensation reaction of the B-H bond for the method of [Et4N][closo-1-CHB9H9] [26], and on the basis of our previous work on the con- synthesis of polyhedral boranes [27–30] and the application of a dihydrogen bond in amine densation reaction of the B-H bond for the synthesis of polyhedral boranes [27–30] and boranes [31–33], we developed a straightforward method for the synthesis of unsolvated the application of a dihydrogen bond in amine boranes [31–33], we developed a straight- forward method for the synthesis of unsolvated potassium and sodium salts of the 11 12 2 path A (1) NaCN (2) conc.HCl (3) NaOH, Me2SO4 NaH path C KOH, HCHO (1) Na,THF (2) BH3.NEt3 180 oC 1,2-DCE, 95 oC CHCl3, Na HCCl3 NaOH BH3.SMe2 path F path DPDF Image | Efficient Way to Directly Synthesize Unsolvated Alkali Metal
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