Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
Kazuma Amaike; Kei Muto; Junichiro Yamaguchi; Kenichiro Itami; Journal of the American Chemical Society 134 (2012) 13573–13576; doi:10.1021/ja306062c

data_4118520
_publ_section_title
;
 Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented
 Nickel Catalysis and Application to the Synthesis of Muscoride A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13573
_journal_page_last               13576
_journal_paper_doi               10.1021/ja306062c
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C63 H104 Ni2 O4 P4'
_chemical_formula_weight         1165.75
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.278(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.497(3)
_cell_length_b                   18.260(4)
_cell_length_c                   17.011(4)
_cell_measurement_reflns_used    6311
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.3458
_cell_measurement_theta_min      3.0178
_cell_volume                     3113.5(13)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20681
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.8956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       Block
_exptl_crystal_F_000             1258
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5466
_refine_ls_number_restraints     127
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+6.7553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                4614
_reflns_number_total             5466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306062c_si_001.cif
_cod_data_source_block           4
_cod_original_cell_volume        3113.7(13)
_cod_database_code               4118520