Nature Synthesis

Table 1 Screening conditions for dimagnesiation of diphenylacetylene (1a)

From: Synthesis of trans-1,2-dimetalloalkenes through reductive anti-dimagnesiation and dialumination of alkynes


Entry	Mg reagent^a	Alkali metal	B electrophile	NMR yield^b (E:Z)
1^c	ⁱPrMgBr	Na dispersion	MeOBpin	90% (57:43)
2^c	ⁱPrMgBr	Na dispersion	EtOBpin	86% (78:22)
3	ⁱPrMgBr	Na dispersion	ⁱPrOBpin	75% (80:20)
4	MeMgBr	Na dispersion	ⁱPrOBpin	49% (47:53)
5	^tBuMgCl	Na dispersion	ⁱPrOBpin	75% (72:28)
6	PhMgBr	Na dispersion	ⁱPrOBpin	71% (41:59)
7	^cPentMgBr	Na dispersion	ⁱPrOBpin	85% (88:12)
8	^cPentMgBr	Na lump	ⁱPrOBpin	25% (76:24)
9	^cPentMgBr	Li granule	ⁱPrOBpin	14% (36:64)
10	^cPentMgBr	Li powder	ⁱPrOBpin	59% (51:49)
11	^cPentMgBr	NaC₁₀H₈	ⁱPrOBpin	74% (91:9)

^aMagnesium reagents were used as a THF solution (∼1 M).
^bYields were determined using ¹H NMR spectroscopy with dibromomethane as an internal standard.
^cThe borylation step was conducted for 1 h. pin, pinacol.

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