Table 1.

Preparation of naphthocycloheptanones through couplling of δ,ε-unsaturated carbene complexes and 2-alkynylbenzoyl systems.

entry	reactants	R1	R2	R3	R4	product	yield %
1	1a + 5a	H	TMSa	Ph	H	7a	77
2	1a + 5b	H	TMSa	H	H	7b	73
3	1b + 5b	Me	TMSa	H	H	7c	75
4	1b + 5c	Me	H	H	H	7c	62
5b	1a + 5d	H	n-Bu	H	H	11	78
6c	1a + 5e	H	CH2OAc	H	H	10	74
7	1a + 5f	H	TMSa	H	OMe	7g	76
8	1b + 5g	Me	TMSa	Me	H	7h	80

^aR² = H in 7 when R² = TMS in 5.

^bThe exclusive product was the alcohol derivative 11.

^cThe exclusive product was elimination product 10.